Dimethylformamide → HCID 68415821, compound

HRID 2098577Notes

Reaction equation

HRID 2098577 reaction equation
[CH:1]1([NH:4][C:5](=[O:24])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.CN(C=O)C.[CH:30]1[CH:31]=[CH:32][C:33]2[N:38](O)N=[N:36][C:34]=2[CH:35]=1.C1(N)C=CC=CC=1N>O>[NH2:38][C:33]1[CH:32]=[CH:31][CH:30]=[CH:35][C:34]=1[NH:36][C:12](=[O:13])[C:11]1[CH:10]=[CH:9][C:8]([CH:7]=[C:6]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[O:24])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 68767501HCID 68767501, compound

Product 1

HCID 68415821HCID 68415821, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4-(3-(cyclopropylamino)-2-(4-methylphenyl)-3-oxoprop-1-en-1-yl)benzoic acid (0.2 g, 0.6 mmol, prepared according to the procedure described in Example 99, step I-III) in DMF (3 mL) EDCl (0.23 g, 1.1 mmol), HOBt (0.08 g, 5 mmol), o-phenylenediamine (0.08 g, 0.7 mmol), were added followed by TEA (0.23 mL, 15 mmol). The reaction mixture was stirred for 4 hours after which the mixture was added to cold water (100 mL) and kept 0° C. for 1 hour to obtain a pale yellow solid. The solid was filtered and washed with water (50 mL) dried under vacuum to afford the title compound (0.110 g, 45% yield). 1H NMR (DMSO-d6) δ (ppm): 0.51 (2H, m, —CH2), 0.63-0.65 (2H, m, —CH2), 2.33 (3H, s, —CH3), 2.67-2.75 (1H, m, —CH), 4.87 (2H, s, —NH2), 6.55-6.58 (1H, m, Ar—H), 6.74-6.76 (1H, m, Ar—H), 6.93-6.97 (1H, m, Ar—H), 7.04 (2H, d, Ar—H), 7.11 (3H, m, Ar—H), 7.19 (2H, m, Ar—H), 7.25 (1H, s, ═CH), 7.76-7.78 (3H, m, Ar—H and —NH), 9.57 (1H, s, —NH), MS m/z: 412.2 (M++1).

Workup

  1. customprepared
  2. waitkept 0° C. for 1 hour
  3. customto obtain a pale yellow solid
  4. filtrationThe solid was filtered
  5. washwashed with water (50 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-5aba41475956439d9f0b98f5db496821
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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