1-Methyl-1H-pyrrole-2-carbaldehyde → HCID 86629536, compound

HRID 1711191Notes

Reaction equation

[NH2:1][CH2:2][C@H:3]([NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]([CH3:32])[CH2:18][CH2:19][NH:20][C:21](=[O:31])[C:22]2[C:27]([CH3:28])=[CH:26][C:25]([Cl:29])=[N:24][C:23]=2[CH3:30])[CH2:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:33][N:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[CH:39]=O.[BH4-].[Na+].[NH4+].[Cl-]>CO>[Cl:29][C:25]1[CH:26]=[C:27]([CH3:28])[C:22]([C:21]([NH:20][CH2:19][CH2:18][CH:17]([N:14]2[CH2:15][CH2:16][CH:11]([NH:10][C@H:3]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:2][NH:1][CH2:39][C:35]3[N:34]([CH3:33])[CH:38]=[CH:37][CH:36]=3)[CH2:12][CH2:13]2)[CH3:32])=[O:31])=[C:23]([CH3:30])[N:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-{3-[4-((R)-2-Amino-1-phenyl-ethylamino)-piperidin-1-yl]-butyl}-6-chloro-2,4-dimethyl-nicotinamide (60 mg, 0.13 mmol) and 1-Methyl-1H-pyrrole-2-carbaldehyde (15 mg, 0.13 mmol) in CH3OH (2 ml) was stirred at rt for 2 h. The mixture was then cooled to 0° C. NaBH4 (8 mg, 0.2 mmol) was added. The mixture was stirred at this temperature for 20 min. NH4Cl (aq. Sat. 1 ml) was then added and the mixture was extracted with CH2Cl2 (3×10 ml). The organic layer was dried and concentrated. Purification of the residue by chromatography on silica gel (CH2Cl2/MeOH, 9:1) afforded 6-chloro-2,4-dimethyl-N-[3-(4-{(R)-2-[(1-methyl-1H-pyrrol-2-ylmethyl)-amino]-1-phenyl-ethylamino}-piperidin-1-yl)-butyl]-nicotinamide (57 mg, 79%).

Workup

extractionthe mixture was extracted with CH2Cl2 (3×10 ml)
customThe organic layer was dried
concentrationconcentrated
customPurification of the residue by chromatography on silica gel (CH2Cl2/MeOH, 9:1)

Sources & evidence

ORD record: ord-6828d7646c634859a1b04020d222df70
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790747B2

Reaction notes

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