(4-Chlorophenyl)acetic acid → HCID 70817765, compound

HRID 82102Notes

Reaction equation

HRID 82102 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH:12]([N:15]1[C:19]2[N:20]=[CH:21][N:22]=[CH:23][C:18]=2[C:17]([C:24]([C:26]2[CH:27]=[N:28][CH:29]=[C:30]([NH:32][CH3:33])[CH:31]=2)=[O:25])=[CH:16]1)([CH3:14])[CH3:13].F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([N:32]([C:30]2[CH:29]=[N:28][CH:27]=[C:26]([C:24]([C:17]3[C:18]4[CH:23]=[N:22][CH:21]=[N:20][C:19]=4[N:15]([CH:12]([CH3:14])[CH3:13])[CH:16]=3)=[O:25])[CH:31]=2)[CH3:33])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 15880(4-Chlorophenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70817679(7-Isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-(methylamino)pyridin-3-yl)methanone

Product 1

HCID 70817765HCID 70817765, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

(4-chlorophenyl)acetic acid (22 mg, 0.13 mmol) was added to a stirring mixture of (7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)[5-(methylamino)pyridin-3-yl]methanone (30 mg, 0.10 mmol) (Preparation 149) and N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylmethanaminium hexafluorophosphate (57 mg, 0.15 mmol) in pyridine (1.0 mL). The mixture was heated to 50° C. for 16 hours, evaporated in vacuo and partitioned between saturated aqueous sodium bicarbonate (10 mL) and EtOAc (10 mL). The aqueous layer was washed with further EtOAc (2×10 mL). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo and purified by preparative HPLC to afford the title compound 43% yield, 19 mg, 1H NMR (400 MHz, DMSO) δ: 1.52 (d, 6H), 3.40 (br. s, 3H), 3.59 (s, 2H), 5.00-5.18 (m, 1H), 7.00-7.42 (m, 4H), 8.21 (s, 1H), 8.50 (s, 1H), 8.86 (s, 1H), 8.90-9.12 (m, 2H), 9.48 (s, 1H);

Workup

  1. customevaporated in vacuo
  2. custompartitioned between saturated aqueous sodium bicarbonate (10 mL) and EtOAc (10 mL)
  3. washThe aqueous layer was washed with further EtOAc (2×10 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f33c36b6e63943f1a970c8a46b5345f0
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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