Dimethylformamide → HCID 50996003, compound

HRID 1772802Notes

Reaction equation

HRID 1772802 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH:17]([N:21]3[CH:25]=[C:24]([C:26]4[C:27]5[CH:34]=[CH:33][NH:32][C:28]=5[N:29]=[CH:30][N:31]=4)[CH:23]=[N:22]3)[CH2:18][C:19]#[N:20])[CH2:12][CH2:11]2)=[O:9])=[N:6][CH:7]=1.[CH3:35][N:36](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]([CH2:18][CH:17]([N:21]1[CH:25]=[C:24]([C:26]2[C:27]3[CH:34]=[CH:33][NH:32][C:28]=3[N:29]=[CH:30][N:31]=2)[CH:23]=[N:22]1)[CH2:16][N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([C:35]#[N:36])=[CH:7][N:6]=2)=[O:9])[CH2:11][CH2:12]1)#[N:20]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 58180965HCID 58180965, compound

Product 1

HCID 50996003HCID 50996003, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

Zinc cyanide (24 mg, 0.20 mmol) and tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.014 mmol) were added to a solution of 4-{4-[(5-bromopyridin-2-yl)carbonyl]piperazin-1-yl}-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile (15 mg, 0.029 mmol) in N,N-Dimethylformamide (0.48 mL). The mixture was degassed, then heated in the microwave at 150° C. for 15 minutes. The mixture was diluted with MeCN (1 mL), filtered and purified via preparative HPLC-MS, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH (9 mg, 67%). 1H NMR (400 MHz, d6-dmso): δ □12.12 (br s, 1H), 9.03 (dd, 1H), 8.81 (s, 1H), 8.68 (s, 1H), 8.43 (dd, 1H), 8.37 (s, 1H), 7.74 (dd, 1H), 7.60 (d, 1H), 6.97 (d, 1H), 4.99 (tt, 1H), 3.62-3.56 (m, 2H), 3.27-3.19 (m, 4H), 2.86 (dd, 1H), 2.82 (dd, 1H), 2.64-2.56 (m, 1H), 2.53-2.41 (m, 2H), 2.39-2.31 (m, 1H); LCMS (M+H)+: 467.3.

Workup

  1. customThe mixture was degassed
  2. additionThe mixture was diluted with MeCN (1 mL)
  3. filtrationfiltered
  4. custompurified via preparative HPLC-MS
  5. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH (9 mg, 67%)

Sources & evidence

ORD record
ord-4571e7c3189e470d9ddd2210ff5cd8a4
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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