2-(Phenylethynyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one → 2-(3-Amino-phenylethynyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

HRID 2298932Notes

Reaction equation

HRID 2298932 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:21](=[O:22])[NH:20][CH2:19][CH2:18][C:17]=2[C:16]=34)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.IC1[NH:25]C2C=CC=C3C(=O)NCCC=1C=23>>[NH2:25][C:5]1[CH:6]=[C:1]([C:7]#[C:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:21](=[O:22])[NH:20][CH2:19][CH2:18][C:17]=2[C:16]=34)[CH:2]=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 98606692-(Phenylethynyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-oneHCID 98832232-Iodo-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

Product 1

HCID 222667022-(3-Amino-phenylethynyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

Procedure

In a manner similar to that described for Example N, Compound 17, 3-ethynyl-analine (129 mg, 1.10 mmol) was coupled to 2-iodo-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one (312 mmol, 1.00 mmol) to yield 2-(3-amino-phenylethynyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 250 mg (83%) as a pale yellow solid: m.p. 261-262° C. (dec); 1H NMR (300 MHz, d6-DMSO) δ3.00 (m, 2H), 3.45 (m, 2H), 5.31 (br s, 2H), 6.63 (m, 1H), 6.71 (m, 1H), 6.76 (m, 1H), 7.08 (app t, J=7.8 Hz, 1H), 7.26 (app t, J=7.8 Hz, 1H), 7.48 (dd, J=8.1, 0.9 Hz, 1H), 7.70 (dd, J=7.5, 0.6 Hz, 1H), 8.09 (br t, 1H), 11.75 (br s, 1H). MS (electrospray, MH+) 302. Anal. (C19H15N3O.0.15 H2O) C, H, N.

Sources & evidence

ORD record
ord-db538e56b76e40128518a1faaf4a68ff
Source dataset
uspto-grants-2002_12
Patent number
US06495541B1

Reaction notes

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