4-(Dimethylcarbamoyl)benzoic acid → HCID 72548866, compound

HRID 63794Notes

Reaction equation

HRID 63794 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8](C(O)=O)=[CH:7][CH:6]=1)=[O:4].C[N:16](C)[C:17](C1C=CC(C(N=[N+]=[N-])=O)=CC=1)=[O:18].[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[N:43]=[C:42]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[C:41]3=[CH:50][C:51]([CH2:53][N:54]([CH3:56])[CH3:55])=[CH:52][N:40]3[N:39]=2)=[CH:34][CH:33]=1>>[CH3:55][N:54]([CH2:53][C:51]1[CH:50]=[C:41]2[N:40]([CH:52]=1)[N:39]=[C:38]([C:35]1[CH:36]=[CH:37][C:32]([NH:31][C:17](=[O:18])[NH:16][C:8]3[CH:7]=[CH:6][C:5]([C:3]([N:2]([CH3:1])[CH3:14])=[O:4])=[CH:13][CH:12]=3)=[CH:33][CH:34]=1)[N:43]=[C:42]2[N:44]1[CH2:45][CH2:46][O:47][CH2:48][CH2:49]1)[CH3:56]

Participants

4

Reactant 3

HCID 110954804-(Dimethylcarbamoyl)benzoic acidHCID 117987912HCID 117987912, compoundHCID 117988571HCID 117988571, compound

Product 1

HCID 72548866HCID 72548866, compoundYield 25.8%

Procedure

According to the general method described in example 13, 4-(dimethylcarbamoyl)benzoic acid was used as starting material, and the resulting 4-(dimethylcarbamoyl)benzoyl azide reacted with 13a to give a light yellow solid (14 mg, 25.8%). m.p. 240° C. 1H NMR (300 MHz, DMSO-d6): δ 9.59 (s, 2H), 8.16 (d, J=8.5 Hz, 2H), 7.99 (s, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.52 (d, J=8.5 Hz, 2H), 7.36 (d, J=8.5 Hz, 2H), 7.19 (s, 1H), 4.25 (s, 2H), 4.08 (t, J=4.4 Hz, 4H), 3.80 (t, J=4.4 Hz, 4H), 2.96 (s, 6H), 2.69 (s, 6H). ESI-MS: 543 (4+1).

Sources & evidence

ORD record
ord-228e93e5721c45b2a884e1d4d427e231
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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