2-[(tert-Butoxycarbonyl)amino]-1,3-benzothiazole-6-carboxylic acid → HCID 87288070, compound

HRID 2043827Notes

Reaction equation

HRID 2043827 reaction equation
Cl.[N:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C@H:5]3[NH2:12])[CH2:3]1)[CH2:9]2.CC(OC([NH:20][C:21]1[S:25][C:24]2[CH:26]=[C:27]([C:30](O)=[O:31])[CH:28]=[CH:29][C:23]=2[N:22]=1)=O)(C)C.ClCCl.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>ClCCl>[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].[N:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C@H:5]3[NH:12][C:30]([C:27]3[CH:28]=[CH:29][C:23]4[N:22]=[C:21]([NH2:20])[S:25][C:24]=4[CH:26]=3)=[O:31])[CH2:3]1)[CH2:9]2

Participants

5

Reactant 3

HCID 27567632-[(tert-Butoxycarbonyl)amino]-1,3-benzothiazole-6-carboxylic acidHCID 21863450Trifluoroacetic acid methylene chlorideHCID 671521221-Azatricyclo[3.3.1.1,3,7]decan-4-amine hydrochloride

Product 1

HCID 87288070HCID 87288070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The protected amide[6-(1-azatricyclo[3.3.1.13,7]dec-4-ylcarbamoyl)-benzothiazol-2-yl)-carbamic acid tert-butyl ester] was prepared from (4r)-1-azatricyclo[3.3.1.13,7]dec-4-ylamine hydrochloride and 2-N-Boc-amino-4-benzothiazole-6-carboxylic acid (Astatech) according to method A. The resulting material was dissolved in dichloromethane (4 mL), treated with dichloromethane-trifluoroacetic acid (4 mL, 1:1), and stirred overnight. After concentrating the reaction mixture under a nitrogen stream, the residue was triturated with ether, and washed with ether and ethyl acetate to afford the title compound; yield 20 mg, 0.03 mmol (43%): 1H NMR (300 MHz, methanol-d4) δ 2.05-2.31 (m, 5H), 2.46 (s, 2H), 3.41-3.61 (m, 4H), 3.83 (d, J=13 Hz, 2H), 4.27 (s, 1H), 7.47 (d, J=8 Hz, 1H), 7.88 (d, J=8 Hz, 1H), 8.23 (s, 1H); MS (DCI/NH3) m/z 329 (M+H)+; Anal. C17H20N4OS.2C2HF3O2: C, H, N.

Workup

  1. concentrationAfter concentrating the reaction mixture under a nitrogen stream
  2. customthe residue was triturated with ether
  3. washwashed with ether and ethyl acetate

Sources & evidence

ORD record
ord-761543fb1515469d9cd7f758df27fa0d
Source dataset
uspto-grants-2013_11
Patent number
US08586746B2

Reaction notes

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