Ammonia → HCID 86726425, compound

HRID 529649Notes

Reaction equation

HRID 529649 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:12])[N:9]([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:14]1[N:15]=[C:16]([O:49][CH3:50])[C:17]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([NH:29]C(=O)OC(C)(C)C)=[C:25]([NH:37]C(=O)[O-])[CH:24]=3)=[CH:21][N:20]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:18]=2[N:19]=1.Cl.N>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[NH:13][C:14]1[N:15]=[C:16]([O:49][CH3:50])[C:17]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([NH2:37])[CH:24]=3)=[CH:21][N:20]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:46])([CH3:48])[CH3:47])[C:18]=2[N:19]=1)[C:8]([N:9]([CH3:11])[CH3:10])=[O:12]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 86726426HCID 86726426, compound

Product 1

HCID 86726425HCID 86726425, compoundYield 78%

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-(2-(2-chloro-4-(dimethylcarbamoyl)phenylamino)-4-methoxy-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-1,2-phenylenedicarbamate (1 equiv) was dissolved in methanolic hydrochloric acid (1N, 7.8 equiv) and stirred at 0° C. overnight. After the reaction was complete, the mixture was basified at 0° C. with aqueous ammonia to pH=7-8 and the aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under reduced pressure gave the crude product, which was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether) to afford the title compound (78% yield). MS (ESI) m/z 582.3 [M+1]+.

Workup

  1. extractionthe aqueous layer was extracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationConcentration under reduced pressure
  6. customgave the crude product, which
  7. customwas purified by silica gel column chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-3735169320944a0985cec93920653836
Source dataset
uspto-grants-2016_05
Patent number
US09346812B2

Reaction notes

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