Acetoacetic Acid → HCID 178436807, compound

HRID 241160Notes

Reaction equation

CC(CC(O)=O)=O.[CH3:8][C:9]1[N:10](C(OCC(C)C)=O)[C:11]2[C:12]([N:28]=1)=[N:13][CH:14]=[C:15]([C:17]1[CH:18]=[CH:19][C:20]3[O:26][CH2:25][CH2:24][NH:23][CH2:22][C:21]=3[CH:27]=1)[CH:16]=2.Cl[C:37]1[C:42]([CH2:43][CH3:44])=[C:41]([CH3:45])[N:40]=[C:39]([CH2:46][N:47]([CH3:49])[CH3:48])[N:38]=1>>[CH2:43]([C:42]1[C:41]([CH3:45])=[N:40][C:39]([CH2:46][N:47]([CH3:49])[CH3:48])=[N:38][C:37]=1[N:23]1[CH2:22][C:21]2[CH:27]=[C:17]([C:15]3[CH:16]=[C:11]4[N:10]=[C:9]([CH3:8])[NH:28][C:12]4=[N:13][CH:14]=3)[CH:18]=[CH:19][C:20]=2[O:26][CH2:25][CH2:24]1)[CH3:44]

Participants

Reactant 3

HCID 96Acetoacetic Acid

HCID 668204282-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate

HCID 79078078HCID 79078078, compound

Product 1

HCID 178436807HCID 178436807, compound

Procedure

Prepared as a diacetate salt by the method of example 6 using 2-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate and 1-(4-chloro-5-ethyl-6-methylpyrimidin-2-yl)-N,N-dimethylmethanamine (reagent preparation 17) in step 3. 1H NMR (400 MHz, DMSO-d6) δ 8.51 (br s, 1H), 8.03 (br s, 1H), 7.67 (d, 1H), 7.52 (dd, 1H), 7.02 (d, 1H), 4.63 (s, 2H), 4.35-4.30 (m, 2H), 3.83-3.78 (m, 2H), 3.32 (s, 2H), 2.65-2.57 (m, 1H), 2.54 (s, 3H), 2.52-2.45 (m, 1H (buried)), 2.36 (s, 3H), 2.10 (s, 6H), 1.86 (s, 8H), 1.15 (t, 3H); MS (EI) for C28H31N7O: 458 (MH+).

Sources & evidence

ORD record: ord-caed9e4115a04502aa5017c1b09239ee
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648066B2

Reaction notes

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