Trifluoroacetic acid → 2-[4-(2,8-Diazaspiro[4.5]dec-2-ylcarbonyl)phenyl]-7-isopropyl-1,3-benzoxazole-5-carbonitrile

HRID 2093653Notes

Reaction equation

C(OC([N:8]1[CH2:39][CH2:38][C:11]2([CH2:15][N:14]([C:16](=[O:37])[C:17]3[CH:22]=[CH:21][C:20]([C:23]4[O:24][C:25]5[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][C:29]([C:35]#[N:36])=[CH:28][C:26]=5[N:27]=4)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:15]1[C:11]2([CH2:38][CH2:39][NH:8][CH2:9][CH2:10]2)[CH2:12][CH2:13][N:14]1[C:16]([C:17]1[CH:18]=[CH:19][C:20]([C:23]2[O:24][C:25]3[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][C:29]([C:35]#[N:36])=[CH:28][C:26]=3[N:27]=2)=[CH:21][CH:22]=1)=[O:37]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of tert-butyl-2-[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]-2,8-diazaspiro[4.5]decane-8-carboxylate (92 mg, 0.174 mmol) in dichloromethane (4 ml) was added trifluoroacetic acid (2 ml, 26.0 mmol). The mixture was stirred for 1 h at 25° C., at which point LC/MS analysis showed the desired amine. The mixture was concentrated and then co-concentrated with toluene to provide the title compound (94 mg, 0.173 mmol, 100% yield). Mass spectrum (ESI) 429.2 (M+).

Workup

concentrationThe mixture was concentrated

Sources & evidence

ORD record: ord-623557ccea6e470bb13e9abb2d73f6d3
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445480B2

Reaction notes

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