Water → HCID 67594115, compound

HRID 343404Notes

Reaction equation

HRID 343404 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]2[CH:24]=[C:23]3[C:19]([C:20]([CH:33]4[CH2:38][CH2:37][N:36]([CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])[CH2:35][CH2:34]4)=[N:21][N:22]3[CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:22]2[C:23]3[C:19](=[CH:18][CH:17]=[C:16](/[CH:15]=[CH:14]/[CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:24]=3)[C:20]([CH:33]3[CH2:38][CH2:37][N:36]([CH2:39][C:40]([OH:42])=[O:41])[CH2:35][CH2:34]3)=[N:21]2)=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67593435HCID 67593435, compound

Product 1

HCID 67594115HCID 67594115, compound

Procedure

4-{2-[3-(1-tert-Butoxycarbonylmethyl-piperidin-4-yl)-1-(4-fluoro-benzyl)-1H-indazol-6-yl]-(E)-vinyl}piperidine-1-carboxylic acid tert-butyl ester (181 mg, 0.29 mmol) was stirred in trifluoroacetic acid (10 ml), containing water (1 ml) at +25° for 2.5 h. The solution was evaporated in vacuo and the residue purified by preparative h.p.l.c. using standard conditions (gradient profile 10-30% (ii) in 1 min, 30% (ii) isochratic for 30 min, 30-10% (ii) in 1 min), but with a flow rate of 20 ml/min. The collected eluant (Rf 21.2 min) was evaporated in vacuo and triturated with ether to give the title compound as a cream solid (80 mg). Analytical h.p.l.c. (gradient profile 10-90% (ii) in 25 min) Rf 12.5 min

Workup

  1. customThe solution was evaporated in vacuo
  2. customthe residue purified by preparative h.p.l.c
  3. customconditions (gradient profile 10-30% (ii) in 1 min, 30% (ii) isochratic for 30 min, 30-10% (ii) in 1 min)
  4. customThe collected eluant (Rf 21.2 min) was evaporated in vacuo
  5. customtriturated with ether

Sources & evidence

ORD record
ord-27bcd20fd43e4d67a2b7b543cbbd26a4
Source dataset
uspto-grants-1999_01
Patent number
US05861414

Reaction notes

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