Pyrrolidine → HCID 70009407, compound

HRID 1266025Notes

Reaction equation

HRID 1266025 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:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=2)=[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([CH2:19][C:18]2[CH:17]=[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]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86758919HCID 86758919, compound

Product 1

HCID 70009407HCID 70009407, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the reductive amination procedure described in Example 82, the title compound was synthesized from 4-(1-oxo-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-6-yl)-benzaldehyde and pyrrolidine in 76% yield as a pale-yellow solid: mp 146-148° C.; 1H NMR (DMSO-d6) δ 1.71 (br s, 4H), 2.49 (br s, 4H), 3.48 (br s, 2H), 3.64 (br s, 2H), 4.30-4.33 (m, 2H), 6.69 (s, 1H), 7.16 (t, 1H, J=9.0 Hz), 7.43 (d, 2H, J=9.0 Hz), 7.55 (d, 2H, J=9.0 Hz), 7.77 (d, 1H, J=9.0 Hz), 7.80 (d, 1H, J=9.0 Hz), 8.38 (t, 1H, J=6.0 Hz). HRMS calcd. for 345.1841 (M+), found 345.1835. Anal. (C22H23N3O.0.25 H2O) C, H, N.

Sources & evidence

ORD record
ord-e5d8c7f3d52e4deba10d507ee73e2626
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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