Diisopropylamine → 4-(2-Fluorophenyl)-7-(isonicotinamido)-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361261Notes

Reaction equation

HRID 2361261 reaction equation
C(O[C:9]([NH:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[F:31])=[CH:23][N:22]=[C:21]([C:32]([OH:34])=O)[C:17]=3[NH:18]2)=[CH:14][CH:13]=1)=[O:10])C1C=CC=CC=1.[Cl-].[NH4+].C([NH:40]C(C)C)(C)C.F[P-](F)(F)(F)(F)F.[N:51]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:55]2C=[CH:57][CH:58]=[CH:59][C:54]=2N=N1.CN1CCOCC1>CN(C=O)C.O>[F:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:24]1[C:16]2[C:15]3[C:19](=[CH:20][C:12]([NH:11][C:9](=[O:10])[C:59]4[CH:58]=[CH:57][N:51]=[CH:55][CH:54]=4)=[CH:13][CH:14]=3)[NH:18][C:17]=2[C:21]([C:32]([NH2:40])=[O:34])=[N:22][CH:23]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 679951827-(Benzyloxycarbonylamino)-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indole-1-carboxylic acid

Product 1

HCID 679956144-(2-Fluorophenyl)-7-(isonicotinamido)-9H-pyrido[3,4-b]indole-1-carboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(benzyloxycarbonylamino)-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indole-1-carboxylic acid (214 mg, 0.470 mmol), ammonium chloride (101 mg, 1.880 mmol), N,N-diisopropylamine (0.394 mL, 2.255 mmol), BOP (270 mg, 0.611 mmol), N-methylmorpholine (0.201 mL, 1.833 mmol) in DMF (2 mL) was stirred at rt for 1 hr. To the reaction solution was added water (20 mL), and the precipitating product (213 mg, 0.422 mmol, 90% yield) was collected as a beige solid by suction filtration and dried over Drierite under vacuum.

Sources & evidence

ORD record
ord-70074d25c5584943891b1110bfff1f75
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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