Phenylacetic Acid → HCID 11744488, compound

HRID 1944541Notes

Reaction equation

HRID 1944541 reaction equation
[N:1]1([C:7]2[CH:25]=[CH:24][C:10]([C:11]([NH:13][C:14]3[CH:15]=[N:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:26]1([CH2:32][C:33](O)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(#N)C>[C:26]1([CH2:32][C:33]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]([C:11]([NH:13][C:14]4[CH:15]=[N:16][C:17]5[C:22]([CH:23]=4)=[CH:21][CH:20]=[CH:19][CH:18]=5)=[O:12])=[CH:24][CH:25]=3)[CH2:6][CH2:5]2)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66815800HCID 66815800, compound

Product 1

HCID 11744488HCID 11744488, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-piperazin-1-yl-N-quinolin-3-yl-benzamide (75 mg, 0.284 mmol), phenylacetic acid (51 mg, 0.375 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU)(118 mg, 0.30 mmol) and N,N—N,N-diisopropylethylamine (0.110 mL, 0.626 mmol) in acetonitrile (2 mL) was heated to 80° C. The solution was cooled to room temperature and the product crystallized. The product was collected by filtration washed with acetonitrile to give 63 mg (49%). MS: m/z 451 (MH+). 1H NMR (DMSO-d6): δ 3.24-3.34 (m, 4 H), 3.63-3.69 (m, 4 H), 3.79 (s, 2 H), 7.05 (d, 2 H), 7.22-7.46 (m, 5 H), 7.54-7.67 (m, 2 H), 7.92-7.99 (m, 4 H), 8.82 (d, 1 H), 9.15 (d, 1 H) and 10.40 (s, 1 H).

Workup

  1. customthe product crystallized
  2. filtrationThe product was collected by filtration
  3. washwashed with acetonitrile
  4. customto give 63 mg (49%)

Sources & evidence

ORD record
ord-8847877316b646c39e683a3e8bd97420
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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