5-Isocyanatoisoquinoline → HCID 10022547, compound

HRID 2056874Notes

Reaction equation

HRID 2056874 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:5][NH2:6].[N:15]([C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[C:21]([CH3:28])[N:22]=[CH:23]2)=[C:16]=[O:17].N(C1C=CC=C2C=1C=CN=C2)=C=O>>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:5][NH:6][C:16]([NH:15][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[C:21]([CH3:28])[N:22]=[CH:23]2)=[O:17]

Participants

4

Reactant 3

HCID 115863575-IsocyanatoisoquinolineHCID 222283825-Isocyanato-3-methylisoquinolineHCID 223377063-Fluoro-4-(1-pyrrolidinyl)benzenemethanamine

Product 1

HCID 10022547HCID 10022547, compound

Procedure

The title compound was prepared using the procedure described in Example 61B using 3-fluoro-4-(1-pyrrolidinyl)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 9.17 (s, 1H), 8.59 (s, 1H), 8.22 (d, 1H, J=7.5 Hz), 7.73 (s, 1H), 7.69 (d, 1H, J=7.5 Hz), 7.50 (t, 1H, J=7.5 Hz), 7.03 (m, 2H), 6.93 (t, 1H, J=6 Hz), 6.72 (m, 1H), 4.24 (d, 2H, J=6 Hz), 3.28 (m, 4H), 2.64 (s, 3H), 1.88 (m, 4H); MS (ESI) 379 (M+H)+; Anal. Calcd for C22H23FN4O: C, 69.82; H, 6.13; N, 14.80. Found: C, 69.76; H, 6.06; N, 14.69.

Sources & evidence

ORD record
ord-4d0cc6ba2b0349f0b61ba3f6c84c873a
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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