Formic Acid → HCID 59239634, compound

HRID 1698024Notes

Reaction equation

HRID 1698024 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][C@@H:33]4[CH3:38])[C:25]4[CH2:31][CH2:30][NH:29][CH2:28][C:26]=4[N:27]=3)=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.N1([O:53][C:54](N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(O)=O.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[N:23]=[C:24]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][C@@H:33]4[CH3:38])[C:25]4[CH2:31][CH2:30][N:29]([CH:54]=[O:53])[CH2:28][C:26]=4[N:27]=3)=[CH:20][CH:21]=2)[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 284Formic AcidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59239135HCID 59239135, compound

Product 1

HCID 59239634HCID 59239634, compound

Procedure

(S)-6-(benzyloxy)-N-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)pyridin-2-amine (0.2684 g, 0.5277 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.226 g, 0.704 mmol) and Formic acid (0.0294 mL, 0.779 mmol) were combined then added dry N,N-Dimethylformamide (2.20 mL, 28.4 mmol) followed by N,N-Diisopropylethylamine (0.507 mL, 2.91 mmol). The reaction mixture stirred for 1 hour then concentrated and chromatographed through silica gel (12 g, 0-5% MeOH in dichloromethane). 1H NMR (500 MHz, DMSO) δ 9.33 (s, 1H), 8.20 (dd, J=7.4, 5.2, 2H), 7.70-7.65 (m, 2H), 7.54 (t, J=7.9, 1H), 7.47 (d, J=7.7, 2H), 7.39 (t, J=7.5, 2H), 7.32 (t, J=7.2, 1H), 6.47 (d, J=7.9, 1H), 6.27 (d, J=7.7, 1H), 5.39 (s, 2H), 4.58 (dt, J=18.2, 12.9, 2H), 4.41 (d, J=19.0, 1H), 4.08 (s, 1H), 3.89 (d, J=11.5, 1H), 3.80-3.51 (m, 5H), 3.44 (s, 1H), 2.73 (s, 1H), 2.69 (s, 1H), 1.30-1.18 (m, 3H). LC/MS-m/z+537.4 (M+H)+.

Workup

  1. concentrationthen concentrated
  2. customchromatographed through silica gel (12 g, 0-5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-34b04c0368fb45abb590ceb7063d681b
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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