4-Methylcyclohexanone → HCID 68004063, compound

HRID 2175595Notes

Reaction equation

[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[NH:9]1[CH2:12][CH:11]([NH:13][C:14](=[O:31])[CH2:15][NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH2:10]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([N:9]2[CH2:10][CH:11]([NH:13][C:14](=[O:31])[CH2:15][NH:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:28])([F:30])[F:29])[CH:25]=4)[N:20]=[CH:19][N:18]=3)[CH2:12]2)[CH2:4][CH2:3]1

Participants

Reactant 3

HCID 115254-Methylcyclohexanone

HCID 5049666Sodium triacetoxyborohydride

HCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Product 1

HCID 68004063HCID 68004063, compound

Procedure

Reaction of 4-methylcyclohexanone with N-(azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide (as prepared in Example 1 Step G) in the presence of TEA and NaBH(OAc)3 as described in Example 1, Step H afforded the product. 1H NMR (CHLOROFORM-d) δ: 8.61 (s, 1 H), 8.11 (s, 1 H), 8.04 (t, J=4.9 Hz, 1 H), 7.71-7.82 (m, 2 H), 6.80 (d, J=7.3 Hz, 1 H), 4.59 (sxt, J=6.4 Hz, 1 H), 4.27 (d, J=5.3 Hz, 2 H), 3.60 (t, J=7.3 Hz, 2 H), 2.95 (t, J=6.6 Hz, 2 H), 2.15 (br. s., 1 H), 1.49-1.61 (m, 1 H), 1.27-1.49 (m, 8H), 0.91 (d, J=6.8 Hz, 3 H); ESI-MS (m/z): Calcd. For C21H26F3N5O: 421.21. found: 422 (M+H).

Workup

customafforded the product

Sources & evidence

ORD record: ord-95d7fa6aa69b402eb92c71b8deb6520c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062048B2

Reaction notes

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