Dimethylformamide → HCID 59239549, compound

HRID 1698022Notes

Reaction equation

HRID 1698022 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:10]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]3[CH3:20])=[N:9][C:8]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=3)=[N:7][C:6]=2[C@@H:5]1[CH3:33])(=[O:3])[CH3:2].C(NC(NC1C=CC(C2N=C(N3CCOC[C@@H]3C)C3CCNC(C)C=3N=2)=CC=1)=O)C.CN(C)C=O.C(N(CC)C(C)C)(C)C.C(Cl)(=O)C>>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:10]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]3[CH3:20])=[N:9][C:8]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=3)=[N:7][C:6]=2[C@H:5]1[CH3:33])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 59239604HCID 59239604, compoundHCID 67178079HCID 67178079, compound

Product 1

HCID 59239549HCID 59239549, compound

Procedure

and 1-(4-((S)-7-acetyl-8-methyl-4-((S)-3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (wr2): 1-Ethyl-3-(4-(8-methyl-4-((S)-3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.172 g, 0.419 mmol) in dry N,N-Dimethylformamide (2.00 mL, 25.8 mmol) was added N,N-Diisopropylethylamine (0.219 mL, 1.26 mmol) followed by Acetyl chloride (0.0448 mL, 0.630 mmol). The reaction mixture was stirred for 2 hours. The reaction mixture was purified by HPLC and the diastereomers were separated by SFC. R-Diastereomer (wr1): 1H NMR (400 MHz, DMSO) δ 8.69 (s, 1H), 8.18 (d, J=8.6, 2H), 7.48 (d, J=8.6, 2H), 6.21 (s, 1H), 3.99 (s, 1H), 3.88 (d, J=12.3, 2H), 3.71 (d, J=10.8, 1H), 3.58 (dd, J=23.8, 11.1, 2H), 3.13 (dd, J=13.5, 6.4, 2H), 3.06-2.91 (m, 3H), 2.71 (t, J=14.7, 1H), 2.38 (d, J=39.3, 1H), 2.12 (d, J=6.4, 3H), 1.58 (d, J=6.8, 1H), 1.47-1.42 (m, 3H), 1.13 (t, J=7.2, 3H), 1.06 (t, J=7.1, 3H). LC/MS-m/z+453.2 (M+H)+; and

Workup

  1. customThe reaction mixture was purified by HPLC
  2. customthe diastereomers were separated by SFC

Sources & evidence

ORD record
ord-ac422f5e363a4755ae1a32f326e7ad87
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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