Hydrochloric Acid → HCID 18381639, compound

HRID 2268905Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16](OC)[CH:17]=2)[C:12](CO)=[N:11][N:10]=1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27]C)[CH3:25].CS(Cl)(=O)=[O:33].N1C[CH2:40][O:39]CC1.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:39][CH3:40])=[CH:16][CH:17]=2)[C:12]([CH2:27][N:26]2[CH2:29][CH2:30][O:33][CH2:25][CH2:24]2)=[N:11][N:10]=1

Participants

Conditions

Temperature: 2 °C

Procedure

A suspension under N2 of [4-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-1-yl]-methanol (1.25 g, 3.6 mmoles), prepared as described in example 103, in CH2Cl2 (30 ml) was added with triethylamine (0.75 ml, 5.4 mmoles). The mixture was cooled to 0-4° C. and dropwise added with methanesulfonyl chloride (0.33 ml, 4.32 mmoles) in CH2Cl2 (5 ml). At the end of the addition the resultant solution was stirred for 1 hour at room temperature, then cooled and added with morpholine (0.94 ml, 10.8 mmoles). The mixture was stirred at room temperature for 3 hours, then poured into 5% HCl. The acidic phase was alkalinised and twice extracted with CH2Cl2, then discoloured with charcoal, filtered over celite and dried to give a foam which was flash chromatographed (eluent: CH2Cl2/CH3OH 98:2). The yielded foam was triturated in ethyl ether to give 1.1 g of the title compound (yield: 52%). m.p.: 202.6-205.6° C.

Workup

temperaturecooled
stirringThe mixture was stirred at room temperature for 3 hours
extractiontwice extracted with CH2Cl2
filtrationfiltered over celite
customdried
customto give a foam which
customchromatographed (eluent: CH2Cl2/CH3OH 98:2)
customThe yielded foam was triturated in ethyl ether

Sources & evidence

ORD record: ord-c28b5a68625045109d7ecebd3587b80a
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329370B1

Reaction notes

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