Trifluoroacetic acid → HCID 11614150, compound

HRID 2301542Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19]([N:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)(=[O:21])=[O:20])[C:13]=1[OH:35])=[O:10].[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19]([N:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]2)(=[O:21])=[O:20])[C:13]=1[OH:35])=[O:10]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 11606774HCID 11606774, compound

Product 1

HCID 11614150HCID 11614150, compoundYield 49%

Procedure

Following the general procedure for Boc deprotection outlined in example 36, N-(2-bromophenyl)-N′-[3-[[4-(tert-butoxycarbonyl)piperazin-1-yl]sulfonyl]4-chloro-2-hydroxyphenyl] urea (10 mg, 0.019 mmol) was stirred in trifluoroacetic acid to form the desired product (5 mg, 49%). 1H NMR (MeOD-d4): δ 8.28 (d, 1H), 7.91 (d, 1H), 7.60 (d, 1H), 7.33 (t, 1H), 7.14 (d, 1H), 7.02 (d, 1H) 3.64 (t, 4H) 3.33 (m, 4H).

Sources & evidence

ORD record: ord-582ede2cf8e44873a2afd3cb0a4f3684
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500863B1

Reaction notes

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