Dimethylformamide → HCID 59239322, compound

HRID 1697932Notes

Reaction equation

HRID 1697932 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3C)[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].C(N(CC)C(C)C)(C)C.CN(C)C=O.[O:44]1[C:48]([C:49](O)=[O:50])=[CH:47][N:46]=[CH:45]1.Cl.CN(C)CCCN=C=NCC>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:16]3[CH2:22][CH2:21][N:20]([C:49]([C:48]4[O:44][CH:45]=[N:46][CH:47]=4)=[O:50])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16340557Oxazole-5-carboxylic AcidHCID 46913570HCID 46913570, compound

Product 1

HCID 59239322HCID 59239322, compound

Procedure

(S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (71 mg, 0.18 mmol) and N,N-diisopropylethylamine (6.0E1 uL, 0.34 mmol) were dissolved in N,N-Dimethylformamide (1.0 mL, 13 mmol). Oxazole-5-carboxylic acid (30.0 mg, 0.265 mmol) 1-hydroxybenzotriazole (27.8 mg, 0.206 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (49.9 mg, 0.260 mmol) were weighed out into a vial, and the solution of the amines was added, then the reaction stirred overnight. The resultant precipitate was removed by filtration and washed with H2O. The resulting solid was purified by reverse phase HPLC: 1H NMR (400 MHz, DMSO) δ 8.68 (s, 1H), 8.63 (s, 1H), 8.19 (d, J=8.4 Hz, 2H), 7.88 (s, 1H), 7.49 (d, J=8.7 Hz, 2H), 6.18 (t, J=5.5 Hz, 1H), 4.98-4.54 (m, 2H), 4.19-4.07 (m, 1H), 4.00-3.54 (m, 7H), 3.48-3.37 (m, 1H), 3.15-3.08 (m, 2H), 2.92-2.65 (m, 2H), 1.26 (d, J=6.6 Hz, 3H), 1.06 (t, J=7.2 Hz, 3H) LC-MS: m/z=+492.2 (M+H)+.

Workup

  1. additionwas added
  2. customThe resultant precipitate was removed by filtration
  3. washwashed with H2O
  4. customThe resulting solid was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-9da0ab8e1dce4ea5827748ae68007c99
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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