Pyrrolidine → HCID 70008125, compound

HRID 1266028Notes

Reaction equation

HRID 1266028 reaction equation
[O:1]=[C:2]1[N:13]2[C:14]3[C:10]([CH:11]=[CH:12]2)=[CH:9][C:8]([C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[CH:18]=O)=[CH:7][C:6]=3[CH2:5][NH:4][CH2:3]1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>O>[N:23]1([CH2:18][C:17]2[CH:16]=[C:15]([C:8]3[CH:9]=[C:10]4[C:14]5=[C:6]([CH2:5][NH:4][CH2:3][C:2](=[O:1])[N:13]5[CH:12]=[CH:11]4)[CH:7]=3)[CH:22]=[CH:21][CH:20]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86758920HCID 86758920, compound

Product 1

HCID 70008125HCID 70008125, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the reductive amination procedure described in Example 82, the title compound was synthesized from 3-(1-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-6-yl)-benzaldehyde and pyrrolidine in 92% yield as a pale-yellow solid: mp 158-160° C.; 1H NMR (DMSO-d6) δ 1.71 (br s, 4H), 2.49 (br s, 4H), 3.49 (br s, 2H), 3.68 (br s, 2H), 4.30-4.33 (m, 2H), 6.70 (s, 1H), 7.17 (t, 1H, J=9.0 Hz), 7.38-7.52 (m, 4H), 7.79 (d, 1H, J=9.0 Hz), 7.82 (d, 1H, J=9.0 Hz), 8.38 (t, 1H, J=6.0 Hz). HRMS calcd. for C22H23N3O 345.1841 (M+), found 345.1848. Anal. (C22H23N3O.0.4 H2O) C, H, N.

Sources & evidence

ORD record
ord-6947fe5be62a4fc391dfd4fb46654275
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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