Dansyl chloride → HCID 10167912, compound

HRID 2237701Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24].[S:32]([Cl:48])([C:35]1[C:47]2[CH:46]=[CH:45][CH:44]=[C:40]([N:41]([CH3:43])[CH3:42])[C:39]=2[CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33]>>[ClH:48].[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:32]([C:35]3[C:47]4[C:39](=[C:40]([N:41]([CH3:43])[CH3:42])[CH:44]=[CH:45][CH:46]=4)[CH:38]=[CH:37][CH:36]=3)(=[O:34])=[O:33])=[C:3]([NH:22][S:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)(=[O:24])=[O:25])[CH:4]=2)[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Participants

Reactant 2

HCID 11801Dansyl chloride

HCID 22272501N-(2-amino-5-(4-t-butyloxycarbonyl-1,4-diazepan-1-yl)-phenyl}benzenesulfonamide

Product 1

HCID 10167912HCID 10167912, compound

Procedure

The compound was synthesized from of N-{2-amino-5-(4-t-butyloxycarbonyl-1,4-diazepan-1-yl)-phenyl}benzenesulfonamide and dansylchloride (73 mg, 0.27 mmol) to give 51 mg AS purple solid. M+ 1 580.3 Calcd 580.20; 1HNMR δ 8.86 (d, 1H), 8.62 (d, 1H), 8.08-7.46 (m, 9H), 6.64 (d, 1H), 6.32 (dd, 1H), 6.14 (d, 1H), 3.53 (app t, 2H), 3.45 (s, 6H), 3.16-3.06 (m, 4H), 2.03-1.95 (m, 2H).

Workup

customto give 51 mg AS purple solid

Sources & evidence

ORD record: ord-35caa32f3add431c8ec1b8661d59afaa
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718650B2

Reaction notes

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