1,2-Dichloroethane → (7S)-2-{[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]carbonyl}-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1623090Notes

Reaction equation

HRID 1623090 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:25][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[C:18]([C:22]([OH:24])=O)[CH:17]=[CH:16]3.[NH:26]1[CH2:31][CH2:30][CH:29]([N:32]2[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[CH2:35][O:34][C:33]2=[O:42])[CH2:28][CH2:27]1.C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[O:42]=[C:33]1[O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[N:32]1[CH:29]1[CH2:30][CH2:31][N:26]([C:22]([C:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][C:12]4[CH2:11][C@:3]5([C:4]6[C:5](=[N:6][CH:7]=[CH:8][CH:9]=6)[NH:10][C:2]5=[O:1])[CH2:25][C:13]=4[CH:14]=3)[N:19]=2)=[O:24])[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 107047401-(Piperidin-4-yl)-1h-benzo[d][1,3]oxazin-2(4h)-oneHCID 59594306HCID 59594306, compound2×

Product 1

HCID 58044750(7S)-2-{[4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidin-1-yl]carbonyl}-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-2-carboxylic acid (15 mg, 0.045 mmol, described in Intermediate 9), 1-piperidin-4-yl-1,4-dihydro-2H-3,1-benzoxazin-2-one (12 mg, 0.045 mmol), EDC (10 mg, 0.050 mmol), HOIST (7 mg, 0.050 mmol), and N,N,N-triethylamine (0.006 mL, 0.045 mmol) was stirred in DMF (2.5 mL) at ambient temperature for 18 h. The reaction mixture was purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions were combined and concentrated to give the title compound. MS: m/z=546 (M+1). HRMS: m/z=546.2132; calculated m/z=546.2136 for C32H28N5O4.

Workup

  1. customThe reaction mixture was purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a8f1d0eaca3e4e0b840c20d4ab0d4792
Source dataset
uspto-grants-2014_07
Patent number
US08778957B2

Reaction notes

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