Sodium Iodide → HCID 178457289, compound

HRID 386699Notes

Reaction equation

HRID 386699 reaction equation
[NH2:1][C:2]1[C:3]([C:10](/[N:12]=[C:13]2/[NH:14][C:15]3([CH2:22][CH2:21][N:20]([C:23]([C:25]4[CH:26]=[C:27]([S:31]([NH:34][CH2:35][C:36]5([C:40]([OH:42])=[O:41])[CH2:39][CH2:38][CH2:37]5)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=4)=[O:24])[CH2:19][CH2:18]3)[CH2:16][NH:17]/2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.Cl[CH2:44][C:45]([N:47]([CH2:51][CH2:52][CH3:53])[CH2:48][CH2:49][CH3:50])=[O:46].C(=O)(O)[O-].[Na+].[Na+].[I-]>CN(C=O)C>[CH2:48]([N:47]([CH2:51][CH2:52][CH3:53])[C:45]([CH2:44][O:41][C:40]([C:36]1([CH2:35][NH:34][S:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:23]([N:20]3[CH2:21][CH2:22][C:15]4([NH:14]/[C:13](=[N:12]/[C:10]([C:3]5[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=5)=[O:11])/[NH:17][CH2:16]4)[CH2:18][CH2:19]3)=[O:24])[CH:26]=2)(=[O:32])=[O:33])[CH2:37][CH2:38][CH2:39]1)=[O:42])=[O:46])[CH2:49][CH3:50]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 2196472-chloro-N,N-dipropylacetamideHCID 516892Sodium BicarbonateHCID 178508766HCID 178508766, compound

Product 1

HCID 178457289HCID 178457289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(3-{2-[(E)-3,5-diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-benzenesulfonylamino)-methyl]-cyclobutanecarboxylic acid (step 2) (350 mg, 0.564 mmol) in DMF (10 ml) was stirred at 50° C. with pre-activated molecular sieves for 30 min. 2-Chloro-N,N-dipropylacetamide (100 mg, 0.564 mmol), sodium bicarbonate (142 mg, 1.693 mmol) and NaI (8.46 mg, 0.056 mmol) were added and stirring continued at 50° C. After 3.5 h, the mixture was allowed to cool to RT and the molecular sieves were removed. The mixture was poured into water and the resulting white suspension was filtered, washed with water and dried in vacuo. The solid was dissolved in DCM and diethyl ether was added to yield a white precipitate which was collected by filtration and dried under vacuum overnight to afford the title product; 1H NMR (400 MHz, DMSO-d6) δ 9.30-7.74 (4H, br hump), 7.88 (1H, d), 7.79 (1H, br s), 7.69 (1H, dd), 7.66 (1H, m), 7.11-6.67 (1H, br hump), 6.84-6.61 (2H, br s), 4.76 (2H, s), 3.82-3.29 (4H, m), 3.44 (2H, s), 3.18-3.14 (4H, m), 3.15 (2H, br s), 2.31-1.95 (4H, m), 1.81 (2H, m), 1.83-1.65 (4H, m), 1.54-1.45 (4H, m), 0.86 (3H, t), 0.80 (3H, t); LC-MS Rt 3.62 mins; 761.7 [M+H]+, Method 10minLC_v003.

Workup

  1. customcontinued at 50° C
  2. customthe molecular sieves were removed
  3. additionThe mixture was poured into water
  4. filtrationthe resulting white suspension was filtered
  5. washwashed with water
  6. customdried in vacuo
  7. dissolutionThe solid was dissolved in DCM
  8. additiondiethyl ether was added
  9. customto yield a white precipitate which
  10. filtrationwas collected by filtration
  11. customdried under vacuum overnight

Sources & evidence

ORD record
ord-8304c9e3b840452d9fd81eaac16cf78d
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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