1-Hydroxybenzotriazole → HCID 18536164, compound
Reaction equation
Cl.Cl.Cl.[C:4]([C:6]1[CH:25]=[CH:24][C:9]([CH2:10][N:11]2[C:15]([CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:14][N:13]=[CH:12]2)=[CH:8][C:7]=1[F:26])#[N:5].[CH:27]([Si:30]([CH:48]([CH3:50])[CH3:49])([CH:45]([CH3:47])[CH3:46])[O:31][C:32]1[CH:41]=[C:40]2[C:35]([CH:36]=[CH:37][CH:38]=[C:39]2[C:42](O)=[O:43])=[CH:34][CH:33]=1)([CH3:29])[CH3:28].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>>[C:4]([C:6]1[CH:25]=[CH:24][C:9]([CH2:10][N:11]2[C:15]([CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([C:42]([C:39]4[C:40]5[C:35](=[CH:34][CH:33]=[C:32]([O:31][Si:30]([CH:45]([CH3:47])[CH3:46])([CH:48]([CH3:50])[CH3:49])[CH:27]([CH3:28])[CH3:29])[CH:41]=5)[CH:36]=[CH:37][CH:38]=4)=[O:43])[CH2:20][CH2:19]3)=[CH:14][N:13]=[CH:12]2)=[CH:8][C:7]=1[F:26])#[N:5]Participants
6
Procedure
The product from Step D (66.1 mg, 0.156 mmol), 7-triisopropylsilyloxy-1-naphthoic acid from Step F (53.8 mg, 0.156 mmol), EDC hydrochloride (33.0 mg, 0.172 mmol), HOBT (23.2 mg, 0.172 mmol), and N,N-diisopropylethylamine (0.136 mL, 0.781 mmol) were stirred in dry, degassed DMF (0.5 mL) at 20° C. overnight. The reaction was stirred overnight and then injected onto a C18 preparative HPLC column and purified with a mixed gradient of 5%-95% acetonitrile/0.1% TFA; 95%-5%/0.1% aqueous TFA over 15 min. The title compound was isolated after conversion to the free base.
Workup
- customin dry
- customdegassed DMF (0.5 mL) at 20° C. overnight
- custompurified with a mixed gradient of 5%-95% acetonitrile/0.1% TFA
- wait95%-5%/0.1% aqueous TFA over 15 min
Sources & evidence
- ORD record
- ord-4b9a32a091874c68b1820c0b7ab203c3
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562823B1
Reaction notes
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