Trifluoroacetic acid → HCID 90041639, compound

HRID 530396Notes

Reaction equation

HRID 530396 reaction equation
C(O)(C(F)(F)F)=O.[C:8]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]2[N:20]=[C:19]([N:21]3[CH2:37][CH2:36][C:24]4([CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)[CH2:23][CH2:22]3)[C:18]([C:38]#[N:39])=[CH:17][N:16]=2)[CH:9]=1>C(Cl)Cl>[C:8]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]2[N:20]=[C:19]([N:21]3[CH2:22][CH2:23][C:24]4([CH2:28][NH:27][CH2:26][CH2:25]4)[CH2:36][CH2:37]3)[C:18]([C:38]#[N:39])=[CH:17][N:16]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90041773HCID 90041773, compound

Product 1

HCID 90041639HCID 90041639, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of the tert-butyl 8-[2-(biphenyl-3-ylamino)-5-cyanopyrimidin-4-yl]-2,8-diazaspiro[4.5]decane-2-carboxylate (24 mg, 0.047 mmol) in CH2Cl2 (1 mL) was added and stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo to afford 2-(biphenyl-3-ylamino)-4-(2,8-diazaspiro[4.5]dec-8-yl)pyrimidine-5-carbonitrile as a white solid. MS ESI calcd. for C25H27N6 [M+H]+ 411, found 411. 1H NMR (400 MHz, DMSO) δ 10.25 (s, 1H), 9.08 (s, 1H), 8.72 (s, 1H), 8.32 (s, 1H), 7.87 (d, 7.9 Hz, 2H), 7.85 (s, 1H), 7.74 (t, J=7.6 Hz, 2H), 7.69-7.59 (m, 2H), 7.57 (d, J=7.8 Hz, 1H), 4.31-4.14 (m, 2H), 4.14-4.04 (m, 2H), 3.65-3.43 (m, 2H), 3.32 (t, J=5.6 Hz, 2H), 2.13 (t, J=7.4 Hz, 2H), 1.94-1.92 (br m, 4H).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-68595bcb7d9344d8b1a9bd93baba449f
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

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