Ammonia → HCID 25152863, compound

HRID 2391572Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[N:17]=[CH:16][C:15]3[N:18]=[CH:19][N:20]([C:21]4[S:25][C:24]([C:26]([O:28]C)=O)=[C:23]([O:30][CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[C:38]([F:41])([F:40])[F:39])[CH:22]=4)[C:14]=3[CH:13]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH3:42]>CO>[C:26]([C:24]1[S:25][C:21]([N:20]2[C:14]3[CH:13]=[C:12]([C:10]([NH:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:11])[N:17]=[CH:16][C:15]=3[N:18]=[CH:19]2)=[CH:22][C:23]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]([F:41])([F:39])[F:40])(=[O:28])[NH2:42]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 150 mg of methyl 5-{6-[(2-morpholin-4-ylethyl)carbamoyl]-1H-imidazo[4,5-c]pyridin-1-yl}-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate (compound B9) and 20 ml of a saturated solution of ammonia in methanol was stirred in a microwave vial at 125° C. for 4 h in the microwave cavity. The reaction mixture was concentrated to dryness, the resulting residue was dissolved in 5 ml of methanol and purified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v)). After lyophilization the title compound was obtained.

Workup

concentrationThe reaction mixture was concentrated to dryness
dissolutionthe resulting residue was dissolved in 5 ml of methanol
custompurified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v))

Sources & evidence

ORD record: ord-2a2c3bbe3fe948f2a29d90347b2f0f13
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

Loading…