Benzenesulfonyl chloride → HCID 86636137, compound

HRID 541595Notes

Reaction equation

HRID 541595 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:46]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38]([CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=[O:39].C(N(CC)C(C)C)(C)C.[C:56]1([S:62](Cl)(=[O:64])=[O:63])[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>CN(C)C=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:46]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38]([CH:40]1[CH2:45][CH2:44][N:43]([S:62]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)(=[O:64])=[O:63])[CH2:42][CH2:41]1)=[O:39]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86636132N-[6-Chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20), 3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]piperidine-4-carboxamide bis(trifluoroacetate)

Product 1

HCID 86636137HCID 86636137, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20), 3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]piperidine-4-carboxamide bis(trifluoroacetate) (10.0 mg, 0.018 mmol) was stirred in N,N-dimethylformamide (1.0 mL) with N,N-diisopropylethylamine (16 μL, 0.089 mmol), and benzenesulfonyl chloride (2.5 μL, 0.020 mmol) was added. Purification by preparative LCMS (pH 2) gave the desired compound (18%). LCMS for C30H30ClN6O3S (M+H)+: m/z=589.2.

Workup

  1. additionwas added
  2. customPurification by preparative LCMS (pH 2)

Sources & evidence

ORD record
ord-4644f23d6bac420d8afed960b8a6b49f
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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