4-Methylmorpholine → HCID 57687105, compound

HRID 908452Notes

Reaction equation

HRID 908452 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:17]1[O:18][C:19]2[C:24]([N:25]=1)=[CH:23][CH:22]=[CH:21][N:20]=2.[CH3:26][N:27]1[CH2:32]CO[CH2:29][CH2:28]1.C[N:34]1C(=O)CCC1>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:34][CH2:29][CH2:28][N:27]([CH3:32])[CH3:26])=[O:14])=[CH:15][CH:16]=2)=[CH:4][C:3]=1[C:17]1[O:18][C:19]2[C:24]([N:25]=1)=[CH:23][CH:22]=[CH:21][N:20]=2

Participants

4

Reactant 3

HCID 79724-MethylmorpholineHCID 13387N-methyl-2-pyrrolidoneHCID 67388520HCID 67388520, compound

Product 1

HCID 57687105HCID 57687105, compound

Procedure

A mixture of 4-(6-amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)benzoic acid (100 mg) N,N-dimethylethane-1,2-diamine (0.036 ml), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (145 mg) and 4-methylmorpholine (0.066 ml) in NMP (1 ml) was stirred at room temperature for 15 hours. The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (5 microns silica, 30 mm diameter, 150 mm length) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions were evaporated to dryness to afford the title compound (38 mg) as a solid; NMR Spectrum: (DMSOd6) 2.19 (s, 6H), 2.42 (t, 2H), 3.35-3.42 (m, 2H), 7.54 (dd, 1H), 7.86 (d, 2H), 7.93 (bs, 2H), 7.95 (d, 2H), 8.30 (dd, 1H), 8.41 (dd, 1H), 8.45 (t, 1H), 8.59 (d, 1H), 8.71 (d, 1H); Mass spectrum: M+H+: 403. RT: 1.73

Workup

  1. customThe reaction mixture was purified by preparative HPLC
  2. customThe fractions were evaporated to dryness

Sources & evidence

ORD record
ord-15981f073a7040e495481aad32cd280e
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

Loading…