1-Hydroxybenzotriazole → [2-(4-{4-[5-(4'-Fluoro-biphenyl-4-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 19605Notes

Reaction equation

HRID 19605 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[F:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([C:55]3[N:60]=[C:59]([NH:61][C:62]4[CH:67]=[CH:66][C:65]([NH2:68])=[CH:64][CH:63]=4)[N:58]4[N:69]=[CH:70][CH:71]=[C:57]4[CH:56]=3)=[CH:51][CH:50]=2)=[CH:45][CH:44]=1>CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15](=[O:17])[NH:68][C:65]2[CH:66]=[CH:67][C:62]([NH:61][C:59]3[N:58]4[N:69]=[CH:70][CH:71]=[C:57]4[CH:56]=[C:55]([C:52]4[CH:53]=[CH:54][C:49]([C:46]5[CH:47]=[CH:48][C:43]([F:42])=[CH:44][CH:45]=5)=[CH:50][CH:51]=4)[N:60]=3)=[CH:63][CH:64]=2)=[CH:18][CH:19]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 166409054-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acidHCID 67319451N-[5-(4'-Fluoro-biphenyl-4-yl)-pyrazolo[1,5-c]pyrimidin-7-yl]-benzene-1,4-diamine2×

Product 1

HCID 67318621[2-(4-{4-[5-(4'-Fluoro-biphenyl-4-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-phenyl)-ethyl]-carbamic acid tert-butyl esterYield 59.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(tert-butoxycarbonylamino-ethyl)-benzoic acid (78 mg) and N-hydroxy-benzotriazole (HOBt)(45 mg) in DMF (5 ml) are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC)(150 mg) and triethylamine (0.27 ml). The mixture is stirred for 0.5 h at ambient temperature. To this solution is added N-[5-(4′-Fluoro-biphenyl-4-yl)-pyrazolo[1,5-c]pyrimidin-7-yl]-benzene-1,4-diamine (compound B4)(0.1 g). After completion of the reaction the mixture is evaporated at high vacuum and the residue is treated with methanol. The resulting solid is filtered and dried. A yellow solid (0.097 g) is obtained.

Workup

  1. customAfter completion of the reaction the mixture
  2. customis evaporated at high vacuum
  3. additionthe residue is treated with methanol
  4. filtrationThe resulting solid is filtered
  5. customdried

Sources & evidence

ORD record
ord-aa35adbbc8be40a9bd00900762ae80f9
Source dataset
uspto-grants-2010_06
Patent number
US07745446B2

Reaction notes

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