Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylate → HCID 67349366, compound

HRID 1676318Notes

Reaction equation

HRID 1676318 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:19](C2C=CC(F)=CC=2)[C:20]([C:22]2([C:25]([NH2:27])=[O:26])[CH2:24][CH2:23]2)=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16](I)[S:17][C:10]=12.[CH2:35]([CH:38]1[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]1)[C:36]#[CH:37]>>[C:25]([C:22]1([C:20]([NH:19][C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]3[CH:14]=[CH:13][N:12]=[C:11]4[CH:15]=[C:16]([C:37]#[C:36][CH2:35][CH:38]5[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]5)[S:17][C:10]=34)=[C:2]([F:1])[CH:3]=2)=[O:21])[CH2:24][CH2:23]1)(=[O:26])[NH2:27]

Participants

3

Reactant 2

HCID 18187546Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylateHCID 67347909N-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

Product 1

HCID 67349366HCID 67349366, compoundYield 49.9%

Procedure

Prepared from N-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (Example 12, Step A, 50 mg, 0.0845 mmol) and tert-butyl 4-(prop-2-ynyl)piperidine-1-carboxylate (37.8 mg, 0.169 mmol) using the procedure described for Example 6, Step B. The reaction was purified by preparative TLC (1 mm thickness, Rf=0.52), eluting with 10% MeOH/DCM. The product was subject to a second preparative TLC purification (0.5 mm thickness, Rf=0.09), eluting with 1:1 EtOA/hexanes. The product was obtained as a beige powder (25 mg, 31%). LRMS (APCI−): m/z 685 (M−1) detected.

Workup

  1. customThe reaction was purified by preparative TLC (1 mm thickness, Rf=0.52)
  2. washeluting with 10% MeOH/DCM
  3. customThe product was subject to a second preparative TLC purification (0.5 mm thickness, Rf=0.09)
  4. washeluting with 1:1 EtOA/hexanes

Sources & evidence

ORD record
ord-8705eb480870491898a7520c71094f6b
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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