Potassium Carbonate → HCID 57741270, compound

HRID 1517667Notes

Reaction equation

HRID 1517667 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]2[C:13]3[N:14]([C:17]4[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=4)[N:15]=[CH:16][C:12]=3[CH2:11][CH2:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.CC(OC([NH:64][CH:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]1)=O)(C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[NH2:64][CH:65]1[CH2:70][CH2:69][N:68]([C:21]([C:20]2[CH:24]=[CH:25][C:17]([N:14]3[C:13]4[C:7]5[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=5[CH2:10][CH2:11][C:12]=4[CH:16]=[N:15]3)=[CH:18][CH:19]=2)=[O:22])[CH2:67][CH2:66]1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86605022HCID 86605022, compound

Product 1

HCID 57741270HCID 57741270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.3 g (0.85 mmol)) 4-(7-acetylamino-4,5-dihydro-pyrazolo[3′,4′:3,4]benzo[1,2-d]thiazol-1-yl)-benzoic acid (prepared analogously to Example 1), 0.32 g (1.00 mmol) TBTU and 0.75 ml (4.38 mmol) diisopropylethylamine in 25 ml dichloromethane is stirred for 15 minutes at ambient temperature and then combined with 0.17 g (0.86 mmol) 4-N-Boc-aminopiperidine. After 2.5 hours the reaction mixture is poured onto 25 ml 5% potassium carbonate solution. The organic phase is dried and evaporated down. The residue is triturated with ethyl acetate/ether.

Workup

  1. customThe organic phase is dried
  2. customevaporated down
  3. customThe residue is triturated with ethyl acetate/ether

Sources & evidence

ORD record
ord-d05d2ff7e8de4f469225a4dc9b70176d
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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