Sodium borohydride → HCID 68183308, compound

HRID 513669Notes

Reaction equation

HRID 513669 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[C:19]([NH2:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[CH:12][CH:11]=2)=O)=[N:6][CH:7]=1.[CH3:21][NH:22][S:23](Cl)(=[O:25])=[O:24].[BH4-].[Na+]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:10]3[CH:11]=[CH:12][C:13]4[C:18](=[N:17][CH:16]=[CH:15][CH:14]=4)[C:19]=3[NH:20][S:23](=[O:25])(=[O:24])[N:22]2[CH3:21])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11789235N-Methylsulfamoyl chloride2×HCID 68183174HCID 68183174, compound2×

Product 1

HCID 68183308HCID 68183308, compoundYield 6.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar fashion using route 27 general procedure 70, 7-[(5-fluoropyridin-2-yl)carbonyl]-8-aminoquinoline (Intermediate 373) (648 mg, 2.4 mmol), N-methylsulfamoyl chloride (Intermediate 213) (942 mg, 7.2 mmol) and NaBH4 (92 mg, 2.4 mmol) in pyridine (10 ml) gave the title compound (57 mg, 2.2%) after purification by preparative HPLC (acidic conditions).

Sources & evidence

ORD record
ord-23293bef6b29481a9add58f8e0217407
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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