Dichloromethane → HCID 67365493, compound

HRID 2046937Notes

Reaction equation

HRID 2046937 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([C:26]([CH3:31])([CH3:30])[C:27](O)=[O:28])[CH:25]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11].[Cl-].C[NH3+].[CH3:35][N:36](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(Cl)Cl>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([C:26]([CH3:30])([CH3:31])[C:27]([NH:36][CH3:35])=[O:28])[CH:25]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 11637Methanamine, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67363896HCID 67363896, compound

Product 1

HCID 67365493HCID 67365493, compound

Procedure

A mixture of 2-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-2-methylpropionic acid (20 mg, 0.04 mmol), methylammonium chloride (14.6 mg, 0.217 mmol), TBTU (28 mg, 0.087 mmol), DIPEA (37.8 μL, 0.217 mmol) and DCM (0.6 mL, 9 mmol) was stirred at rt for 1 h. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography (eluent: 2% MeOH in DCM) to give desired product. MS (ES+): m/z 474.09, 476.03 (100, 90) [MH+]. HPLC: tR=3.45 min (ZQ3 polar—5 min). 1H NMR (400 MHz, CD3OD): δ=1.81 (s, 6H), 1.88 (d, J=7.3 Hz, 3H), 2.71 (s, 3H), 5.29 (q, J=7.2 Hz, 1H), 7.14-7.23 (m, 1H), 7.36 (d, J=1.5 Hz, 1H), 7.43 (s, 2H), 7.65 (s, 1H), 8.00 (s, 1H), 8.39 (br. s., 1H).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe resulting residue was purified by a flash chromatography (eluent: 2% MeOH in DCM)

Sources & evidence

ORD record
ord-e14bb4edb2254317a5b24250ee614bee
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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