4-Bromoaniline → HCID 178422742, compound

HRID 1898361Notes

Reaction equation

HRID 1898361 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[NH:8][C:9]1[NH:10][C:11]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[C:15]([C:23]([OH:25])=O)=[CH:14][C:12]=2[N:13]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[Br:61][C:62]1[CH:68]=[CH:67][C:65]([NH2:66])=[CH:64][CH:63]=1>C1COCC1.CN(C=O)C>[Br:61][C:62]1[CH:68]=[CH:67][C:65]([NH:66][C:23]([C:15]2[C:16]3[O:20][C:19]([CH3:22])([CH3:21])[CH2:18][C:17]=3[C:11]3[NH:10][C:9]([NH:8][C:7]4[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=4[Cl:26])=[N:13][C:12]=3[CH:14]=2)=[O:25])=[CH:64][CH:63]=1

Participants

7

Reactant 4

HCID 78074-BromoanilineHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178422814HCID 178422814, compound

Product 1

HCID 178422742HCID 178422742, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-3, 0.070 g, 0.177 mmol), benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (0.157 g, 0.355 mmol), N-methyl morpholine (0.5 mL), DMF (1.0 mL), THF (5.0 mL) and 4-bromo aniline (0.092 g, 0.531 mmol) to afford 0.010 g of the desired product. 1HNMR (DMSO-d6): δ 1.23 (s, 3H), 1.57 (s, 3H), 3.06 (s, 2H), 7.24 (s, 1H), 7.52 (d, J=8.7 Hz, 2H), 7.68 (d, J=8.7 Hz, 2H), 8.44 (s, 2H), 9.72 (s, 1H), 10.98 (s, 1H), 11.52 (s, 1H); MS [M−H]−: 546.22.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-9ab2557351b6476bbfae8eadaada0856
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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