Trifluoroacetic acid → phenylmethyl [6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridin-2-yl]carbamate

HRID 473892Notes

Reaction equation

[C:1]1([CH2:7][O:8][C:9]([NH:11][C:12]2[NH:13][C:14]3[C:15]([N:38]=2)=[N:16][CH:17]=[C:18]([C:20]2[CH:21]=[CH:22][C:23]4[O:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][C:24]=4[CH:37]=2)[CH:19]=3)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[O:29]1[C:23]2[CH:22]=[CH:21][C:20]([C:18]3[CH:19]=[C:14]4[NH:13][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:7][C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[N:38][C:15]4=[N:16][CH:17]=3)=[CH:37][C:24]=2[CH2:25][NH:26][CH2:27][CH2:28]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1,1-dimethylethyl 7-[2-({[(phenylmethyl)oxy]carbonyl}amino)-1H-imidazo[4,5-b]pyridin-6-yl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (0.49 g, 1.9 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (10 mL) and the resulting solution was heated at 50° C. After 1 h the reaction mixture was concentrated and the residue was concentrated three times from ethyl acetate (30 mL) to afford phenylmethyl [6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridin-2-yl]carbamate as the bis-trifluoroacetate salt (0.48 g, 95% yield). MS (EI) for C23H21N5O3: 416 (MH+).

Workup

concentrationAfter 1 h the reaction mixture was concentrated
concentrationthe residue was concentrated three times from ethyl acetate (30 mL)

Sources & evidence

ORD record: ord-8395f20e7de84cd8b6104759e2bdb643
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637499B2

Reaction notes

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