Dimethylformamide → HCID 68415976, compound

HRID 2098586Notes

Reaction equation

HRID 2098586 reaction equation
[CH:1]1([NH:4][C:5](=[O:32])[C:6]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)=[CH:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.CN(C=O)C.[CH:38]1[CH:39]=[CH:40][C:41]2[N:46](O)N=[N:44][C:42]=2[CH:43]=1.C1(N)C=CC=CC=1N>O>[NH2:44][C:42]1[CH:43]=[CH:38][CH:39]=[CH:40][C:41]=1[NH:46][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:23]([CH2:22][NH:21][C:18]2[CH:17]=[CH:16][C:15]([C:6]([C:5]([NH:4][CH:1]3[CH2:3][CH2:2]3)=[O:32])=[CH:7][C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=3)=[CH:20][CH:19]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 68418414HCID 68418414, compound

Product 1

HCID 68415976HCID 68415976, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4-((4-(3-(cyclopropylamino)-1-(4-fluorophenyl)-3-oxoprop-1-en-2-yl)phenylamino)methyl)benzoic acid (0.215 g, 0.5 mmol) in DMF (3 mL) EDCl (0.23 g, 1.1 mmol), HOBt (0.08 g, 0.55 mmol), o-phenylene diamine (0.086 g, 0.7 mmol), were added followed by TEA (0.2 mL, 1.5 mmol). The reaction mixture was stirred for 4 hours after which the mixture was added to cold water (100 mL) and kept at 0° C. for 1 hour. The pale yellow solid formed was filtered and washed with ethyl acetate (15 mL) dried under vacuum to afford the title compound (0.020 g, 8% yield). 1H NMR (DMSO-d6) δ (ppm): 0.46-0.47 (2H, m, —CH2), 0.60-0.62 (2H, m, —CH2), 2.70-2.71 (1H, m, —CH), 4.36-4.37 (2H, d, —CH2), 4.88 (2H, s, —NH2), 6.55-6.61 (4H, m, Ar—H and —NH), 6.76-6.82 (3H, m, Ar—H), 6.93-6.94 (1H, t, Ar—H), 6.98-7.04 (3H, m, Ar—H), 7.06-7.17 (3H, m, Ar—H), 7.48-7.50 (3H, m, Ar—H and ═CH), 7.93-7.95 (2H, d, Ar—H and —NH), 9.61 (1H, s, —NH), MS m/z: 521.1 (M++1).

Workup

  1. additionwere added
  2. waitkept at 0° C. for 1 hour
  3. customThe pale yellow solid formed
  4. filtrationwas filtered
  5. washwashed with ethyl acetate (15 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-e58cd596b26946a5a742735f62cec382
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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