Ammonia → HCID 71609382, compound

HRID 1507645Notes

Reaction equation

Cl[C:2]1[C:3]2[S:10][CH:9]=[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:21]([C:23]4[NH:27][C:26]([S:28]([CH3:31])(=[O:30])=[O:29])=[N:25][C:24]=4[C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)=[O:22])[CH:17]=[CH:16][C:15]=3[CH3:39])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:40].CC(O)C>>[NH2:40][C:2]1[C:3]2[S:10][CH:9]=[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:21]([C:23]4[NH:27][C:26]([S:28]([CH3:31])(=[O:30])=[O:29])=[N:25][C:24]=4[C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)=[O:22])[CH:17]=[CH:16][C:15]=3[CH3:39])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 3776Isopropanol

HCID 86729700HCID 86729700, compound

Product 1

HCID 71609382HCID 71609382, compoundYield 59%

Conditions

Temperature: 80 °C

Procedure

Compound 4-chloro-N-(5-(4-(4-fluorophenyl)-2-(methylsulfonyl)-1H-imidazole-5-carboxamido)-2-methylphenyl)thieno[3,2-d]pyrimidine-7-carboxamide (7.0 mg, 0.01 mmol) was dissolved into 2M ammonia in IPA (1.0 mL, 1.99 mmol ammonia). The resulting solution was heated in a sealed vial at 80° C. for 6 hrs. The solvent was removed under reduced pressure and the crude material was purified by SiO2 chromatography (DCM to 8% MeOH gradient, desired product elutes in 6% MeOH) (4 mg, 59% yield). 1HNMR (400 MHz, MeOD/CDCl3): d 8.64 (s, 1H), 8.42 (s, 1H), 8.26 (m, 1H), 7.66 (m, 2H), 7.56 (m, 2H), 7.51 (s, 1H), 7.41 (m, 2H), 7.07 (d, 1H, J=9.2 Hz), 7.01 (t, 2H, J=8.4 Hz), 3.20 (s, 3H), 2.33 (s, 3H). MS (ESI): m/z 565.9 [M+H]+.

Workup

customThe solvent was removed under reduced pressure
customthe crude material was purified by SiO2 chromatography (DCM to 8% MeOH gradient, desired product elutes in 6% MeOH) (4 mg, 59% yield)

Sources & evidence

ORD record: ord-2853dcf0355c4ff1bd43308a373040bf
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221805B2

Reaction notes

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