Diisopropylethylamine → HCID 135431014, compound

HRID 1531669Notes

Reaction equation

HRID 1531669 reaction equation
[CH:1]([O:4][S:5]([C:8]1[C:17]([N:18]=[N:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:16]([OH:28])[C:15]2[C:10](=[CH:11][C:12]([NH2:29])=[CH:13][CH:14]=2)[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:39][O:40][C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([O:50][CH3:51])[CH:49]=1)[C:44](Cl)=[O:45]>ClCCl>[CH:1]([O:4][S:5]([C:8]1[C:17]([N:18]=[N:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:16]([OH:28])[C:15]2[C:10](=[CH:11][C:12]([NH:29][C:44](=[O:45])[C:43]3[CH:47]=[C:48]([O:50][CH3:51])[CH:49]=[C:41]([O:40][CH3:39])[CH:42]=3)=[CH:13][CH:14]=2)[CH:9]=1)(=[O:6])=[O:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 870033,5-Dimethoxybenzoyl chlorideHCID 135494401HCID 135494401, compound

Product 1

HCID 135431014HCID 135431014, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Amino-4-hydroxy-3-(4-methoxy-phenylazo)-napthalene-2-sulfonic acid isopropyl ester (Example 6, 200 mg, 0.48 mmol ) was dissolved in dichloromethane (3 mL) and diisopropylethylamine (160 μL, 114 mg, 0.96 mmol ) was added. 3,5-Dimethoxybenzoyl chloride (111 mg, 0.6 mmol ) was added under nitrogen. The reaction mixture was allowed to stir for 16 h. The suspension was filtered to provide the title compound (110 mg, 0.19 mmol, 40% ) as a red solid: NMR (DMSO-d6): δ 10.72 (s, 1H). 8.46 (s, 1H), 8.32 (d, 9 Hz, 1H), 8.05 ( d, 9 Hz, 1H), 7.80 (d, 9 Hz, 3H), 7.12 (m, 4H), 6.79 (s, 1H), 4.86 (m, 1H), 3.86 (m, 9H), 1.22 (d, 6 Hz, 6H). Analytical HPLC: 87% pure. MS (ES-NEG): [M−H] 578; Anal. Calc. for C29H29N3O8S: C, 60.09, H, 5.04, N, 7.25. Found: C, 57.60, H, 5.17, N, 6.88.

Workup

  1. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-8f5af286a59841848d9abadb0ad1a0d5
Source dataset
uspto-grants-2001_03
Patent number
US06200963B1

Reaction notes

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