Ammonia → 2-[(2'-methyl-2',3'-dihydro-1'H-spiro[cyclopropane-1,4'-isoquinolin]-7'-yl)amino]-6-(2-methylphenyl)-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.[C:52]1([CH3:60])[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[NH:58][NH2:59].CNN.N>>[CH3:12][N:13]1[CH2:22][C:21]2([CH2:24][CH2:23]2)[C:20]2[C:15](=[CH:16][C:17]([NH:25][C:27]3[N:28]=[CH:29][C:8]4[C:9](=[O:10])[N:58]([C:53]5[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=5[CH3:60])[N:59]=[C:1]([C:45]5[CH:46]=[CH:47][CH:48]=[CH:50][CH:51]=5)[C:7]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:14]1Participants
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 o-tolylhydrazine for methylhydrazine in Example 6D. MS (DCI/NH3) m/z 501 (M+H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 1.04-1.25 (m, 4H), 2.19 (s, 3H), 3.35-3.47 (m, 2H), 4.23 (s, 2H), 6.80 (d, J=8.4 Hz, 1H), 7.38-7.45 (m, 4H), 7.52-7.59 (m, 4H), 7.69 (s, 1H), 7.88 (d, J=4.0 Hz, 2H), 9.42 (s, 1H), 10.71 (s, 1H), 11.33 (s, 1H).
Sources & evidence
- ORD record
- ord-206e244c6b384fe49622134156c9c530
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051327B2
Reaction notes
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