Hydrochloric Acid → HCID 68863569, compound

HRID 1725957Notes

Reaction equation

HRID 1725957 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH:15][S:16]([C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22])(=[O:18])=[O:17])=[O:4].CN1CCOCC1.[CH3:35][N:36]([CH3:42])[CH2:37][CH2:38][CH2:39][NH:40][CH3:41].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH3:35][N:36]([CH3:42])[CH2:37][CH2:38][CH2:39][N:40]([CH3:41])[C:21]([C:20]1[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=1[S:16]([NH:15][C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[C:3]([O:2][CH3:1])=[O:4])(=[O:18])=[O:17])=[O:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 2733179PyBroPHCID 68863930HCID 68863930, compound

Product 1

HCID 68863569HCID 68863569, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 149B (102 mg, 0.264 mmol) in dichloromethane (1.0 mL) was treated with 4-methylmorpholine (87 μL, 0.792 mmol), 4-dimethylaminopyridine (3 mg, 0.025 mmol), N,N,N′,-trimethyl-1,3-propanediamine (42.6 μL, 0.290 mmol), and bromotripyrrolidinophosphonium hexafluorophosphate (123.3 mg, 0.265 mmol), stirred at room temperature for 3 days, and treated with 1N HCl. The aqueous layer was extracted with ethyl acetate three times and the combined organic phases were washed with brine, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(+)) m/e 484 (M+H)+; (ESI(−)) m/e 482 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.49 (s, 1H), 9.26 (s, 1H), 8.02 (d, 1H), 7.94 (dd, 1H), 7.1 (dd, 1H), 7.72 (dt, 1H), 7.61-7.48 (m, 5H), 3.84 (s, 3H), 3.19 (br s, 2H), 3.07 (m, 2H), 2.82 (d, 6H), 2.67 (s, 3H), 1.98 (quint, 2H).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate three times
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-42a8396db9eb4ff5a1d095e6ab66bc3b
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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