Dichloromethane → HCID 67252250, compound

HRID 1711709Notes

Reaction equation

HRID 1711709 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:17]=[C:16]([C:27]#[N:28])[CH:15]=2)=[O:12])[N:7]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)[Cl:47]>>[ClH:47].[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:17]=[C:16]([C:27]#[N:28])[CH:15]=2)=[O:12])[N:7]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH2:35][NH:34][CH2:33][CH2:32]3)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 67253817HCID 67253817, compound

Product 1

HCID 67252250HCID 67252250, compoundYield 93%

Procedure

In CH2Cl2 (8 mL) was placed tert-butyl 6-(3-tert-butyl-5-(3-(3-cyano-5-(pyridin-3-yloxy)phenyl)ureido)-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (83 mg, 0.14 mmol). HCl (g) was bubbled into reaction mixture until the solution was saturated and the solution was then stirred at RT for 4 hrs. Concentration in vacuo gave a solid which was triturated with ether (10 mL). The solid was collected by filtration, washed with ether (2 mL) and dried to afford 1-(3-tert-butyl-1-(1,2,3,4-tetrahydroisoquinolin-6-yl)-1H-pyrazol-5-yl)-3-(3-cyano-5-(pyridin-3-yloxy)phenyl)urea hydrochloric acid salt (69 mg, 93% yield). 1H NMR (300 MHz, DMSO-d6) δ 1.26 (s, 9H), 3.06-3.09 (m, 2H), 3.35-3.40 (m, 2H), 4.28-4.30 (m, 2H), 6.33 (s, 1H), 7.23-7.24 (m, 1H), 7.31-7.34 (m, 1H), 7.39-7.47 (m, 4H), 7.63-7.67 (m, 2H), 7.77-7.78 (m, 1H), 8.52-8.54 (m, 1H), 8.59 (m, 1H), 8.93 (s, 1H), 9.42-9.43 (m, 2H), 10.16 (s, 1H); MS (ESI) m/z: 527.2 (M+H+).

Workup

  1. customHCl (g) was bubbled into reaction mixture until the solution
  2. concentrationConcentration in vacuo
  3. customgave a solid which
  4. customwas triturated with ether (10 mL)
  5. filtrationThe solid was collected by filtration
  6. washwashed with ether (2 mL)
  7. customdried

Sources & evidence

ORD record
ord-d6eaa5b08b0749ed81f7d57f00b97602
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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