Trifluoroacetic acid → 2-(2-(3-((1,4-diazepan-1-yl)methyl)benzamido)-5-(piperidin-1-yl)-phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

HRID 625356Notes

Reaction equation

[F:1][C:2]([F:56])([F:55])[C:3]1[CH:4]=[C:5]([CH:52]=[CH:53][CH:54]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:19]=[CH:18][C:17]=2[NH:28][C:29]([C:31]2[CH:32]=[C:33]([CH:49]=[CH:50][CH:51]=2)[CH2:34][N:35]2[CH2:41][CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37][CH2:36]2)=[O:30])[CH:11]=1)=[O:9].FC(F)(F)C(O)=O>ClCCl>[N:35]1([CH2:34][C:33]2[CH:32]=[C:31]([CH:51]=[CH:50][CH:49]=2)[C:29]([NH:28][C:17]2[CH:18]=[CH:19][C:20]([N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)=[CH:21][C:16]=2[C:12]2[CH:11]=[C:10]([CH:15]=[CH:14][N:13]=2)[C:8]([NH:7][CH2:6][C:5]2[CH:52]=[CH:53][CH:54]=[C:3]([C:2]([F:55])([F:56])[F:1])[CH:4]=2)=[O:9])=[O:30])[CH2:41][CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1

Participants

Conditions

Temperature: 15 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 4-(3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzyl)-1,4-diazepane-1-carboxylate (100 mg, 0.13 mmol, 1.00 equiv) in dichloromethane (15 mL), and trifluoroacetic acid (147.9 mg, 1.30 mmol, 10.00 equiv). The resulting solution was stirred for 3 h at 15° C. The resulting mixture was concentrated under vacuum to yield 130 mg of crude product as a red solid.

Workup

customInto a 50-mL round-bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-37879fda5ca3418d90b668f60f10beb0
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09301951B2

Reaction notes

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