Methylamine → HCID 70008909, compound

HRID 1266024Notes

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.[CH3:23][NH2:24]>>[CH3:23][NH:24][CH2:19][C:18]1[CH:17]=[CH:16][C:15]([C:8]2[CH:9]=[C:10]3[C:14]4=[C:6]([CH2:5][NH:4][CH2:3][C:2](=[O:1])[N:13]4[CH:12]=[CH:11]3)[CH:7]=2)=[CH:22][CH:21]=1

Participants

Reactant 2

HCID 6329Methylamine

HCID 86758919HCID 86758919, compound

Product 1

HCID 70008909HCID 70008909, compoundYield 71%

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 methylamine in 71% yield as a pale-yellow solid: mp 178-180° C.; 1H NMR (DMSO-d6) δ 2.29 (s, 3H), 3.48 (br s, 2H), 3.70 (s, 2H), 4.30-4.33 (m, 2H), 6.68 (s, 1H), 7.16 (t, 1H, J=9.0 Hz), 7.45 (d, 2H, J=6.0 Hz), 7.55 (d, 2H, J=6.0 Hz), 7.77 (d, 1H, J=9.0 Hz), 7.80 (d, 1H, J=9.0 Hz), 8.36 (t, 1H, J=6.0 Hz). HRMS calcd. for C19H19N3O 305.3828 (M+), found 305.1536. Anal. (C19H19N3O.0.1H2O) C, H, N.

Sources & evidence

ORD record: ord-c21d1fd6316c4e2db1d1382b93e6dbb3
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548494B1

Reaction notes

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