Hydrochloric Acid → HCID 178439345, compound

HRID 1276106Notes

Reaction equation

Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CC(C)([O-])C.[K+].[C:12]([CH2:15][CH2:16][CH:17]([CH:19]1[C:35]2([CH3:36])[CH:22]([CH:23]3[CH:32]([CH2:33][CH:34]2[OH:37])[C:31]2([CH3:38])[CH:26]([CH2:27][CH:28]([O:39][CH2:40][CH2:41][NH:42][C:43]4[C:48]([F:49])=[CH:47][C:46]([CH:50]=[C:51]([CH3:57])[C:52](OCC)=[O:53])=[CH:45][C:44]=4[F:58])[CH2:29][CH2:30]2)[CH2:25][CH:24]3[OH:59])[CH2:21][CH2:20]1)[CH3:18])([OH:14])=[O:13].Cl>CN(C=O)C.CO.C(O)(=O)C.O.O>[F:49][C:48]1[CH:47]=[C:46]([CH:50]=[C:51]([CH3:57])[C:52]([NH:4][C:3]([NH2:5])=[NH:2])=[O:53])[CH:45]=[C:44]([F:58])[C:43]=1[NH:42][CH2:41][CH2:40][O:39][CH:28]1[CH2:27][CH:26]2[C:31]([CH3:38])([CH:32]3[CH:23]([CH:24]([OH:59])[CH2:25]2)[CH:22]2[C:35]([CH3:36])([CH:19]([CH:17]([CH3:18])[CH2:16][CH2:15][C:12]([OH:14])=[O:13])[CH2:20][CH2:21]2)[CH:34]([OH:37])[CH2:33]3)[CH2:30][CH2:29]1

Participants

Conditions

Temperature: 112.5 °C

Procedure

130 mg of guanidine hydrochloride and 125 mg of potassium t-butoxide are stirred at RT for 30 minutes in 1 ml of anhydrous DMF. A solution of 150 mg of ethyl 3-(4-{2-[17-(3-carboxy-1-methylpropyl)-7,12-dihydroxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-3-yloxy]ethylamino}-3,5 -difluorophenyl)-2-methylacrylate in 1 ml of anhydrous DMF is then added and the mixture is stirred at 110-115° C. for 6 hours. The reaction mixture is then poured onto 100 ml of water, adjusted to pH=6 using aqueous HCl solution and the product is filtered off. It is dried in a fine vacuum and 8.0 mg of an amorphous solid are obtained. Rf (CH2C12 /MeOH/acetic acid/water 32:8:1:1)=0.21 MS (ES): 689 (M+H)+

Workup

filtrationthe product is filtered off
dry with materialIt is dried in a fine vacuum and 8.0 mg of an amorphous solid
customare obtained

Sources & evidence

ORD record: ord-b9c2527f3d1b46518a787907e1233ca2
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166002

Reaction notes

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