Ammonia → 6-allyl-2-[(2'-methyl-2',3'-dihydro-1'H-spiro[cyclopropane-1,4'-isoquinolin]-7'-yl)amino]-8-phenylpyrimido[4,5-d]pyridazin-5(6H)-one
Reaction equation
[C:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])C=CC=CC=1.[CH3:12][N:13]1[CH2:22][C:21]2([CH2:24][CH2:23]2)[C:20]2[C:15](=[CH:16][C:17]([NH2:25])=[CH:18][CH:19]=2)[CH2:14]1.[NH:26]=[C:27]1C2C(=NC=NC=2)N[C:29](=O)[NH:28]1.CN1CCN([C:45]2[CH:51]=[CH:50][C:48](N)=[CH:47][CH:46]=2)CC1.[CH2:52]([NH:55][NH2:56])[CH:53]=[CH2:54].CNN.N>>[CH2:52]([N:55]1[C:9](=[O:10])[C:8]2[CH:29]=[N:28][C:27]([NH:25][C:17]3[CH:16]=[C:15]4[C:20]([C:21]5([CH2:24][CH2:23]5)[CH2:22][N:13]([CH3:12])[CH2:14]4)=[CH:19][CH:18]=3)=[N:26][C:7]=2[C:1]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:50][CH:51]=2)=[N:56]1)[CH:53]=[CH2:54]Participants
Reactant 7
Product 1
Procedure
The title compound was prepared as described in Example 6, substituting benzoyl chloride for 3-phenylpropanoyl chloride in Example 6B, 2′-methyl-2′,3′-dihydro-1′H-spiro[cyclopropane-1,4′-isoquinolin]-7′-amine (Furukawa, S.; Ikeno, T.; Kato, S.; Kawasaki, M.; Kojima, H.; Minagawa, W.; Sawada, N.; Yamamoto, F.; Lohani, S.; Wang, Y. Process for preparation of a 3,4-dihydro-4-imino-pyrimido[4,5-d]pyrimidin-2(1H)-one derivative. WO 2009151997) for 4-(4-methylpiperazin-1-yl)aniline in Example 6C, and allylhydrazine for methylhydrazine in Example 6D. MS (DCI/NH3) m/z 451 (M+H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 0.91-1.26 (m, 4H), 2.89 (s, 3H), 3.21-3.30 (m, 1H), 3.41-3.51 (m, 1H), 4.22 (s, 2H), 4.78 (d, J=5.2 Hz, 2H), 5.21 (s, 1H), 5.24 (d, J=2.8 Hz, 1H), 6.01-6.08 (m, 1H), 6.79 (d, J=8.4 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.54-7.62 (m, 3H), 7.65 (s, 1H), 7.86 (d, J=6.4 Hz, 2H), 9.37 (s, 1H), 10.63 (s, 1H), 11.07 (s, 1H).
Sources & evidence
- ORD record
- ord-60c2d8c878e944fc88c4e90ff9bc169a
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051327B2
Reaction notes
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