1-Hydroxybenzotriazole → HCID 66736072, compound

HRID 1640996Notes

Reaction equation

HRID 1640996 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:16]=[C:15]3[NH:40][C:41](=[O:51])[C:42]2[CH:50]=[CH:49][C:45]([C:46](O)=[O:47])=[CH:44][CH:43]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[N:74]1([CH:79]2[CH2:84][CH2:83][NH:82][CH2:81][CH2:80]2)[CH2:78][CH2:77][CH2:76][CH2:75]1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([C:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:16]=[C:15]3[NH:40][C:41](=[O:51])[C:42]2[CH:50]=[CH:49][C:45]([C:46]([N:82]3[CH2:83][CH2:84][CH:79]([N:74]4[CH2:78][CH2:77][CH2:76][CH2:75]4)[CH2:80][CH2:81]3)=[O:47])=[CH:44][CH:43]=2)(=[O:10])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 787034-(1-Pyrrolidinyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66736201HCID 66736201, compound

Product 1

HCID 66736072HCID 66736072, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The crude N-[5-(3,5-difluoro-benzenesulfonyl)-1-trityl-1H-indazol-3-yl]-terephthalamic acid (0.56 mmol) was treated with dichloromethane (8 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (140 mg, 1.3 eq), 1-hydroxybenzotriazole (98 mg, 1.3 eq) and 4-pyrrolidin-1-yl-piperidine (113 mg, 1.3 eq). The reaction mixture was stirred at room temperature overnight, diluted with dichloromethane, washed with brine and with a saturated solution of sodium hydrogenocarbonate, dried over sodium sulfate and evaporated to dryness affording the crude title compound that was used as such for the next step without further purification.

Workup

  1. washwashed with brine and with a saturated solution of sodium hydrogenocarbonate
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-c52fa87b017549328b2636d17a58fee8
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

Loading…