3-Fluorobenzylamine → HCID 18442000, compound

HRID 458412Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=2)[C:8]2[C:18](=[O:19])[N:17]3[CH2:20][CH2:21][CH2:22][N:16]3[C:9]=2[NH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].[F:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH2:37]>>[F:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH:37][C:27]([C:26]1[CH:30]=[CH:31][C:23]([C:7]2[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([C:12]([F:14])([F:15])[F:13])[N:10]=[C:9]3[N:16]4[CH2:22][CH2:21][CH2:20][N:17]4[C:18](=[O:19])[C:8]=23)=[CH:24][CH:25]=1)=[O:29]

Participants

Reactant 2

HCID 668533-Fluorobenzylamine

HCID 18441949HCID 18441949, compound

Product 1

HCID 18442000HCID 18442000, compound

Procedure

The product from Step A was treated as described in Step E of Example 8 followed by coupling to 3-fluorobenzylamine as described in Step F of Example 8 to provide the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 9.19 (t, 1H, J=6), 7.93 (d, 2H, J=8), 7.45 (d, 2H, J=8), 7.35 (dd, 1H, J=14, 8), 7.14 (m, 2H), 7.05 (t, 1H, J=9), 4.49 (d, 2H, J=6), 3.98 (m, 4H), 3.84 (t, 2H, J=7), 2.60 (quint., 2H, J=7), 0.91 (t, 3H, J=7) ppm; ; ESI-MS m/z 543 (M+H)+; Anal. calcd. for C27H22F4N4O4.⅓H2O: C, 59.12; H, 4.17; N, 10.21; found: C, 59.12; H, 4.14; N, 10.26.

Sources & evidence

ORD record: ord-0a9b634c87d845b18ddafa27fcabe54c
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189851B2

Reaction notes

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