5-Isocyanatoisoquinoline → HCID 11741004, compound

HRID 887251Notes

Reaction equation

HRID 887251 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[N:16]([C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[C:22]([CH3:29])[N:23]=[CH:24]2)=[C:17]=[O:18].N(C1C=CC=C2C=1C=CN=C2)=C=O>>[CH3:29][C:22]1[N:23]=[CH:24][C:25]2[C:20]([CH:21]=1)=[C:19]([NH:16][C:17]([NH:13][CH2:12][C:11]1[CH:10]=[CH:9][C:8]([N:5]3[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:15][CH:14]=1)=[O:18])[CH:28]=[CH:27][CH:26]=2

Participants

4

Reactant 3

HCID 115863575-IsocyanatoisoquinolineHCID 176089301-[4-(4-Methylpiperidin-1-yl)phenyl]methanamineHCID 222283825-Isocyanato-3-methylisoquinoline

Product 1

HCID 11741004HCID 11741004, compound

Procedure

The title compound was prepared using the procedure described in Example 61B using 4-(4-methyl-1-piperidinyl)benzylamine and the product from Example 154A instead of 4-cyanobenzyl alcohol and the product from Example 61A. 1H NMR (300 MHz, DMSO-d6) δ 9.70 (s, 1H), 9.66 (s, 1H), 8.74 (s, 1H), 8.59 (d, 1H, J=8.7 Hz), 8.01 (d, 1H, J=8.7 Hz), 7.82 (m, 2H), 7.65 (m, 2H), 7.48 (m, 2H), 4.40 (d, 2H, J=6 Hz), 3.54 (m, 4H), 2.78 (s, 3H), 1.90-1.50 (m, 5H), 0.98 (d, 3H, J=6 Hz); MS (ESI) 389 (M+H)+; Anal. Calcd for C24H28N4O.2.6HCl: C, 59.64; H, 6.38; N, 11.59. Found: C, 59.31; H, 6.39; N, 11.19.

Sources & evidence

ORD record
ord-d7925238b972469d8002c31c4672c7d2
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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