Hydrochloric Acid → HCID 57860920, compound

HRID 644252Notes

Reaction equation

HRID 644252 reaction equation
N[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:31]=[C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:29]=[CH:28][C:7]=1[C:8]([NH:10][C:11]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:12]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1)=[O:14])=[O:9].[CH2:38]=O.[C:40]([BH3-])#[N:41].[Na+].Cl>C(Cl)Cl.CC(O)=O.CO>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:11]=2[NH:10][C:8](=[O:9])[C:7]2[CH:28]=[CH:29][C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:31][C:6]=2[O:5][CH2:4][CH2:3][CH2:2][N:41]([CH3:40])[CH3:38])=[N:17][CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57860910HCID 57860910, compound

Product 1

HCID 57860920HCID 57860920, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-(3-aminopropoxy)-4-(morpholin-4-yl)benzoylamino]-N-(5-chloropyridin-2-yl)-5-fluorobenzamide (400 mg, 0.76 mmol), paraformaldehyde (96 mg, 3.19 mmol) and MeOH (75 mL) was adjusted to pH 5-6 with AcOH. Sodium cyanoborohydride (96 mg, 1.57 mmol) was added. After stirring overnight, the reaction was acidified with 1 N HCl (pH=2) and stirred for 2 hours. Methylene chloride was added to the mixture and it was basified with 50% satd Na2 CO3. The organic layer was dried (Na2 SO4) and concentrated to give the desired product (418 mg, 99%).

Workup

  1. stirringstirred for 2 hours
  2. customThe organic layer was dried (Na2 SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-29204688cb1b4a19aa9869a9ac51ef7d
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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