Diisopropylethylamine → HCID 66604256, compound

HRID 2410804Notes

Reaction equation

HRID 2410804 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:8]([C:11]1[C:16]2[NH:17][C:18]3[CH:19]=[C:20]([C:24](O)=[O:25])[CH:21]=[CH:22][C:23]=3[C:15]=2[N:14]=[C:13]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=1)(=[O:10])[NH2:9].C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CO.C(#N)C>[O:1]1[CH2:7][CH2:6][CH2:5][N:4]([C:24]([C:20]2[CH:21]=[CH:22][C:23]3[C:15]4[N:14]=[C:13]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:12]=[C:11]([C:8]([NH2:9])=[O:10])[C:16]=4[NH:17][C:18]=3[CH:19]=2)=[O:25])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 218732751,4-OxazepaneHCID 66605825HCID 66605825, compound

Product 1

HCID 66604256HCID 66604256, compoundYield 73.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 1,4-oxazepane (15 mg, 0.15 mmol), 4-carbamoyl-2-phenyl-5H-pyrido[3,2-b]indole-7-carboxylic acid (50 mg, 0.15 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.071 mL, 0.41 mmol) in dry DMF (1.3 mL) was stirring for a few minutes and then benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (80 mg, 0.18 mmol) was added. After 1 hr, the reaction was diluted with MeOH and preparative HPLC (PHENOMENEX® Luna 30×100 mm C18, Solvent A=10% acetonitrile -90% H2O—0.1% TFA; Solvent B=90% acetonitrile—10% H2O —0.1% TFA, 10-70% B gradient over 18 min) afforded 7-(1,4-oxazepane-4-carbonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide (45 mg, 0.11 mmol, 70% yield) as a yellow solid. MS (ESI) m/z 415.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.75 (1H, br. s.), 8.65 (1H, br. s.), 8.50 (1H, s), 8.31 (3H, d, J=7.63 Hz), 7.92 (1H, br. s.), 7.78 (1H, br. s.), 7.56 (2H, t, J=7.63 Hz), 7.45 (1H, t, J=7.32 Hz), 7.28 (1H, d, J=7.63 Hz), 3.77 (5H, br. s.), 3.65 (1H, br. s.), 3.50 (2H, br. s.), 1.94 (1H, br. s.), 1.79 (1H, br. s.).

Sources & evidence

ORD record
ord-cc69c9b16dd3414a84a3f65ce470b26f
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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