Formic Acid → HCID 86614444, compound

HRID 1038087Notes

Reaction equation

HRID 1038087 reaction equation
[CH:1](O)=[O:2].[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([NH2:54])([C:16](=[O:53])[NH:17][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([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)[N:22]=[C:21]3[C:46]2[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=2)[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([C:16](=[O:53])[NH:17][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23]([C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:22]=[C:21]3[C:46]2[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=2)([NH:54][CH:1]=[O:2])[CH2:12]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 67420202HCID 67420202, compound

Product 1

HCID 86614444HCID 86614444, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Formic acid (17 mg, 0.36 mmol) was added to a solution of 3-Amino-3-[3-(4-fluoro-phenyl)-1 trityl-indazol-5-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1P) 250 mg, 0.367 mmol); 2-Chloro-4,6-dimethoxy-1,3,5-triazine (77 mg, 0.44 mmol); DMAP (10 mg) and NMM (50 mg, 0.49 mmol) in MeCl2 (3 ml) at room temperature. The solvent was evaporated and residue chromatographed on silica gel eluting with 3% v/v MeOH/MeCl2 yielding 4P as a white solid (210 mg, 80%) ESMS (MH 710).

Workup

  1. customat room temperature
  2. customThe solvent was evaporated
  3. customresidue chromatographed on silica gel eluting with 3% v/v MeOH/MeCl2 yielding 4P as a white solid (210 mg, 80%) ESMS (MH 710)

Sources & evidence

ORD record
ord-cc30f77ec71c40b59b498d570bce976f
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…