Hydrochloric Acid → HCID 53378896, compound

HRID 627435Notes

Reaction equation

HRID 627435 reaction equation
C(OC([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][N:11]([C:18]1[CH:19]=[N:20][C:21]([NH:24][C:25]3[N:26]=[CH:27][C:28]4[CH:33]=[C:32]([C:34](=[O:38])[N:35]([CH3:37])[CH3:36])[N:31]([CH:39]5[CH2:43][CH2:42][CH2:41][CH2:40]5)[C:29]=4[N:30]=3)=[CH:22][CH:23]=1)[C:12](=[O:17])[CH2:13]2)=O)(C)(C)C.C(OCC)(=O)C.Cl>O1CCOCC1>[CH3:36][N:35]([CH3:37])[C:34]([C:32]1[N:31]([CH:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)[C:29]2[N:30]=[C:25]([NH:24][C:21]3[CH:22]=[CH:23][C:18]([N:11]4[C:12](=[O:17])[CH2:13][CH:14]5[NH:8][CH:9]([CH2:16][CH2:15]5)[CH2:10]4)=[CH:19][N:20]=3)[N:26]=[CH:27][C:28]=2[CH:33]=1)=[O:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 67375795HCID 67375795, compound

Product 1

HCID 53378896HCID 53378896, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 0.55 grams (0.96 mmoles) of 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-4-oxo-3,9-diaza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester was added 15 ml of ethyl acetate. The mixture was stirred at room temperature under N2 and cooled to ice bath temperature. To this mixture was added 5 mls 4N HCl in dioxane. The resultant mixture was allowed to stir until all starting material was consumed. The resultant mixture was stirred until all starting material was consumed as determined by HPLC-MS. To this mixture was added 50 ml of a 1:1 mixture of ethyl acetate/diethyl ether to precipitate solids. The solids were filtered and washed with excess 1:1 mixture of ethyl acetate/diethyl ether and dried under vacuum to a constant weight to yield 7-Cyclopentyl-2-[5-(4-oxo-3,9-diaza-bicyclo[4.2.1]non-3-yl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide as the di-hydrochloride salt, 0.213 grams (45% yield). MS m/z 489 (M+H)+. 1H NMR (400 MHz, D6 DMSO) δ 10.2 (s, 1H, broad), 9.05 (s, 1H, broad), 8.35 (s, 1H), 8.0 (d, 1H), 7.7 (d, 1H), 6.9 (s, 1H), 4.82 (m, 1H, broad), 4.6 (d, 1H), 4.25 (s, 1H, broad), 4.15 (s, 1H, broad), 3.82 (m, 1H, broad), 3.5 (d, 1H), 3.05 (s, 6H), 2.82 (m, 1H), 2.3 (m, 2H), 2.2-1.95 (m, 10H, broad), 1.89 (m, 1H), 1.65 (m, 2H).

Workup

  1. temperaturecooled to ice bath temperature
  2. stirringto stir until all starting material
  3. customwas consumed
  4. stirringThe resultant mixture was stirred until all starting material
  5. customwas consumed
  6. additionTo this mixture was added
  7. addition50 ml of a 1:1 mixture of ethyl acetate/diethyl ether
  8. customto precipitate solids
  9. filtrationThe solids were filtered
  10. washwashed with excess 1:1 mixture of ethyl acetate/diethyl ether
  11. customdried under vacuum to a constant weight

Sources & evidence

ORD record
ord-e7ee83f15ce34ba5b45c4e3aa11930ad
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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