Methanol → HCID 59285970, compound

HRID 1011589Notes

Reaction equation

[CH3:1][NH2:2].CO.[NH2:5][C:6]([NH:8][C:9]1[NH:10][C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[C:12]([CH:17]=O)[C:13]=1[C:14]([NH2:16])=[O:15])=[O:7].[BH4-].[Na+]>O1CCCC1.CC(C)=O>[NH2:5][C:6]([NH:8][C:9]1[NH:10][C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[C:12]([CH2:17][NH:2][CH3:1])[C:13]=1[C:14]([NH2:16])=[O:15])=[O:7]

Participants

Conditions

Temperature: 40 °C

Procedure

40% Methylamine in methanol (1 mL, 9.8 mmol) was added to a suspension of 2-aminocarbonylamino-5-(3-chlorophenyl)-4-formylpyrrole-3-carboxamide (Compound No. 17-1, 45 mg, 0.15 mmol) in tetrahydrofuran (1 mL), and the mixture was sealed and stirred at 40° C. for 3 hours. Moreover, sodium borohydride (25 mg, 0.66 mmol) was added thereto and the whole was stirred at room temperature for 3 hours. Acetone (5 mL) was added to the reaction solution and concentrated in vacuo. Water (10 mL) was added to the obtained residue, and the precipitated solid was filtered off. The solid was washed with water (10 mL) and the mixed solvent (5.5 mL), which consists of chloroform and ethanol (10:1), dried under reduced pressure to give the target compound (17 mg) as an orange solid (Yield 36%).

Workup

stirringthe whole was stirred at room temperature for 3 hours
concentrationconcentrated in vacuo
additionWater (10 mL) was added to the obtained residue
filtrationthe precipitated solid was filtered off
washThe solid was washed with water (10 mL)
customdried under reduced pressure

Sources & evidence

ORD record: ord-704f5882e5dc4447a2db744339cf7535
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977371B2

Reaction notes

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