HCID 66697928, compound → HCID 66760644, compound

HRID 389594Notes

Reaction equation

HRID 389594 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[N:12][N:13]=[CH:14]3)O1.[NH2:20][C:21]1[N:22]=[CH:23][C:24]([C:31]2[CH:32]=[N:33][N:34]([CH:36]3[CH2:41][CH2:40][N:39]([C:42](=[O:44])[CH3:43])[CH2:38][CH2:37]3)[CH:35]=2)=[C:25]2[CH:29]=[C:28](Cl)[O:27][C:26]=12>>[NH2:20][C:21]1[N:22]=[CH:23][C:24]([C:31]2[CH:32]=[N:33][N:34]([CH:36]3[CH2:37][CH2:38][N:39]([C:42](=[O:44])[CH3:43])[CH2:40][CH2:41]3)[CH:35]=2)=[C:25]2[CH:29]=[C:28]([C:9]3[CH:18]=[CH:17][CH:16]=[C:15]4[C:10]=3[CH:11]=[N:12][N:13]=[CH:14]4)[O:27][C:26]=12

Participants

3

Reactant 2

HCID 66697928HCID 66697928, compoundHCID 66759397HCID 66759397, compound

Product 1

HCID 66760644HCID 66760644, compoundYield 3%

Procedure

The title compound was prepared in 3% yield from 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phthalazine and 1-{4-[4-(7-amino-2-chlorofuro[2,3-c]pyridin-4-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone, by a procedure analogous to Example 223, Step D. The sample underwent both mass-directed purification and preparative TLC during purification. 1H NMR (400 MHz, CD3OD): δ 10.32 (s, 1H), 9.73 (s, 1H), 8.63 (dd, J=0.76, 7.58 Hz, 1H), 8.32 (d, J=8.08 Hz, 1H), 8.18-8.25 (m, 2H), 7.96-8.03 (m, 2H), 7.76 (s, 1H), 4.67-4.76 (m, 1H), 4.55-4.61 (m, 1H), 3.35-3.42 (m, 1H), 2.88 (dt, J=2.65, 12.95 Hz, 1H), 2.21-2.31 (m, 2H), 2.19 (s, 3H), 1.98-2.18 (m, 3H); MS (ESI): 454.19 [M+H]+; HPLC tR=0.85 min (TOF: polar—3 min).

Workup

  1. customThe sample underwent both mass-directed purification and preparative TLC
  2. customduring purification
  3. customHPLC tR=0.85 min (TOF: polar—3 min)

Sources & evidence

ORD record
ord-b8fd8ade4f1f4b02a59cd14f4ec562ad
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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