Methanesulfonic Acid → HCID 58529408, compound

HRID 1972892Notes

Reaction equation

HRID 1972892 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:23]3[CH:24]=[CH:25][C:26]4[C:30]([CH:31]=3)=[N:29][N:28]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:27]=4)[CH:9]=[C:10]([C:11]([C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][NH:19][CH2:20]4)=[CH:15][CH:14]=3)=O)[N:6]2[N:5]=[CH:4][N:3]=1.CS(O)(=O)=O>ClCCl>[CH2:32]([N:28]1[CH:27]=[C:26]2[C:30]([CH:31]=[C:23]([C:8]3[CH:9]=[C:10]([CH2:11][C:13]4[CH:22]=[C:21]5[C:16]([CH2:17][CH2:18][NH:19][CH2:20]5)=[CH:15][CH:14]=4)[N:6]4[C:7]=3[C:2]([NH2:1])=[N:3][CH:4]=[N:5]4)[CH:24]=[CH:25]2)=[N:29]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 58529969HCID 58529969, compound

Product 1

HCID 58529408HCID 58529408, compoundYield 617.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[4-Amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-(1,2,3,4-tetrahydro-isoquinolin-7-yl)-methanone (0.050 g, 0.01 mmol) was dissolved in dichloromethane (1 mL) and methanesulfonic acid (0.104 mL, 1.61 mmol) was added followed by Et3SIH (0.128 mL, 0.80 mmol). The resulting mixture was stirred at rt overnight. The mixture was diluted with dichloromethane and washed with saturated aqueous NaHCO3, water and brine. The organic layer was concentrated, suspended in MeOH and filtered to give a desired product as white solid (30 mg, 62%). 1H-NMR (CD3OD-d4) 8.28-8.24 (m, 1 H), 7.78 (s, 1 H), 7.70 (dd, 1H), 7.59-7.56 (m, 1 H), 7.33-7.23 (m, 5 H), 7.11 (dd, 1 H), 7.07-6.89 (m, 3 H), 6.39 (s, 1 H), 5.57 (s, 2 H), 4.16 (s, 2 H), 3.82 (s, 2 H), 2.96 (t, 2 H), 2.71 (t, 2 H); LC-MS [M+H]+=486.3, RT=2.30 min.

Workup

  1. washwashed with saturated aqueous NaHCO3, water and brine
  2. concentrationThe organic layer was concentrated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d6cc11e3a0214fa0b9fe615b04304a77
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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