1,1'-Carbonyldiimidazole → HCID 11376158, compound

HRID 2117360Notes

Reaction equation

[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20]4=[N:21][CH:22]=[C:23]([C:25]([OH:27])=O)[CH:24]=[C:19]4[N:18]=[CH:17]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.CCN(C(C)C)C(C)C.[N:53]1([CH2:59][CH2:60][NH2:61])[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1>C1COCC1>[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20]4=[N:21][CH:22]=[C:23]([C:25]([NH:61][CH2:60][CH2:59][N:53]5[CH2:58][CH2:57][O:56][CH2:55][CH2:54]5)=[O:27])[CH:24]=[C:19]4[N:18]=[CH:17]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-{4-[(4-(trifluoromethoxy)benzyl)oxy]phenyl}-3H-imidazo[4,5-b]pyridine-6-carboxylic acid (42 mg, 0.1 mmol), CDI (32.4 mg, 0.2 mmol) and DIPEA (87 μL, 0.5 mmol) in dry THF (2 mL) was stirred at 60° C. for 2 h and then treated with 2-(morpholin-4-yl)ethylamine (26 μL, 0.2 mmol). After a further 2 h at 60° C. the mixture was concentrated in vacuo and the residue chromatographed over silica gel eluting with 5% MeOH/CHCl3 to give 3-{4-[(4-(trifluoromethoxy)benzyl)oxy]phenyl}-N-(2-morpholin-4-ylethyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide. 1H NMR (400 MHz, D4-MeOH) δ 2.57 (br.s, 4H), 2.65 (t, J=8 Hz, 2H), 3.60 (t, J=8 Hz, 2H), 3.71 (t, J=8 Hz, 4H), 5.21 (s, 2H), 7.22 (dd, J=6.8 and 2 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 7.59 (d, J=8.8 Hz, 2H), 7.71 (dd, J=6.8 and 2 Hz, 2H), 8.57 (d, J=1.6 Hz, 1H), 8.71 (s, 1H) and 8.90 (d, J=1.6 Hz, 1H); MS (ES+): m/z 542 [MH+].

Workup

concentrationAfter a further 2 h at 60° C. the mixture was concentrated in vacuo
customthe residue chromatographed over silica gel eluting with 5% MeOH/CHCl3

Sources & evidence

ORD record: ord-8d040d2a3e7d4c1abf36ecdd935c0c1a
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442709B2

Reaction notes

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