Cyclobutanone → HCID 24743881, compound

HRID 1947417Notes

Reaction equation

HRID 1947417 reaction equation
[N:1]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:26](=[O:27])[CH:25]=[CH:24][CH:23]=[N:22]4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][C@@H:3]2[CH2:6][NH:7][CH2:8][C@H:2]12.[C:28]1(=O)[CH2:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH:28]1([N:7]2[CH2:6][C@@H:3]3[C@@H:2]([N:1]([C:9]4[CH:14]=[CH:13][C:12]([C:15]5[CH:20]=[CH:19][C:18]([N:21]6[C:26](=[O:27])[CH:25]=[CH:24][CH:23]=[N:22]6)=[CH:17][CH:16]=5)=[CH:11][CH:10]=4)[CH2:5][CH2:4]3)[CH2:8]2)[CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 673963272-(4'-((3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)biphenyl-4-yl)pyridazin-3(2H)-one

Product 1

HCID 24743881HCID 24743881, compound

Procedure

The product from Example 85B (0.033 g, 0.092 mmol), cyclobutanone (8.00 μL, 0.101 mmol), and sodium triacetoxyborohydride (0.025 g, 0.0.120 mmol) were processed as described in Example 85C to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.91 (d, J=1.7 Hz, 1H), 7.63 (s, 4H), 7.50 (d, J=8.5 Hz, 2H), 7.23 (d, J=3.7 Hz, 1H), 7.07 (d, J=8.8 Hz, 1H), 6.65 (d, J=8.5 Hz, 2H), 4.13-4.24 (m, 1H), 3.52 (q, 1H), 3.32 (q, J=7.3 Hz, 1H), 2.74-3.04 (m, 3H), 2.63 (t, 1H), 2.46 (dd, J=9.3, 2.2 Hz, 1H), 2.35 (dd, J=8.8, 4.4 Hz, 1H), 2.06-2.23 (m, 1H), 1.82-2.05 (m, 4H), 1.60-1.80 (m, 3H). MS (ESI+) m/z 413 (M+H)+.

Sources & evidence

ORD record
ord-e08b9fcfec1e48899d98636f16ebb5c1
Source dataset
uspto-grants-2013_03
Patent number
US08399468B2

Reaction notes

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