Trifluoroacetic acid → HCID 68708606, compound

HRID 645517Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[C:22]([C:23](=[O:32])[NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:21]([NH:33][CH2:34][CH:35]3[CH2:42][CH2:41][C:38]4([CH2:40][CH2:39]4)[CH2:37][CH2:36]3)[N:20]=[C:19]([C:43]#[N:44])[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:25]([NH:24][C:23]([C:22]1[C:17]([O:16][CH2:15][CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[N:18][C:19]([C:43]#[N:44])=[N:20][C:21]=1[NH:33][CH2:34][CH:35]1[CH2:36][CH2:37][C:38]2([CH2:39][CH2:40]2)[CH2:41][CH2:42]1)=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(2-{5-benzylcarbamoyl-2-cyano-6-[(spiro[2.5]oct-6-ylmethyl)amino]-pyrimidin-4-yloxy}ethyl)piperidine-1-carboxylic acid tert-butyl ester (0.68 mmol) in CH2Cl2 (10 mL) is added TFA (2 mL) at 0° C. After stirring for 2 h at 0° C. under N2 atmosphere, the mixture is concentrated and dried in vacuo to give 2-cyano-4-(2-piperidin-4-yl-ethoxy)-6-[(spiro[2.5]oct-6-ylmethyl)amino]pyrimidine-5-carboxylic acid benzyl amide as a yellow solid. 1H-NMR (CDCl3), δ 0.17-0.30 (4H, m), 0.89-0.93 (2H, m), 1.00-1.11 (2H, m), 1.14-1.24 (2H, m), 1.29-1.38 (1H, m), 1.51-1.81 (9H, m), 2.41-2.48 (2H, m), 2.99-3.02 (2H, m), 3.42 (2H, t), 4.45 (2H, t), 4.56 (2H, d), 7.29-7.39 (5H, m), 8.17 (1H, t), 10.16 (1H, t).

Workup

concentrationthe mixture is concentrated
customdried in vacuo

Sources & evidence

ORD record: ord-e4e6e7b8d97648f08db20a75e9316cae
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704996B2

Reaction notes

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