1-Hydroxybenzotriazole → HCID 23001315, compound

HRID 398014Notes

Reaction equation

HRID 398014 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:13]3[C:14]([C:17]([OH:19])=O)=[CH:15][N:16]=[C:12]3[CH2:11][CH2:10]2)=[CH:5][C:4]=1[F:20])#[N:2].[Si:21]([O:38][C:39]1[CH:40]=[C:41]([CH2:45][CH2:46][CH2:47][CH2:48][NH2:49])[CH:42]=[CH:43][CH:44]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>>[Si:21]([O:38][C:39]1[CH:40]=[C:41]([CH2:45][CH2:46][CH2:47][CH2:48][NH:49][C:17]([C:14]2[N:13]3[CH:9]([C:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:20])[CH:5]=4)[CH2:10][CH2:11][C:12]3=[N:16][CH:15]=2)=[O:19])[CH:42]=[CH:43][CH:44]=1)([C:34]([CH3:35])([CH3:36])[CH3:37])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23001304HCID 23001304, compoundHCID 70025062HCID 70025062, compound

Product 1

HCID 23001315HCID 23001315, compound

Procedure

Carboxylic acid from Step K, Example 5 (13.4 mg, 0.0496 mmol), amine from Step D (20.0 mg, 0.0496 mmol), EDC hydrochloride (19.0 mg, 0.0991 mmol), HOBT (13.4 mg, 0.0991 mmol), and N,N-diisopropylethylamine (0.0432 mL, 0.248 mmol) were stirred in dry, degassed DMF (1 mL) at 25° C. for 16 hours. The reaction was poured onto aq. NaHCO3 (10 mL) and extracted with methylene chloride (3×10 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to provide the title compound as a white solid.

Workup

  1. customin dry
  2. customdegassed DMF (1 mL) at 25° C. for 16 hours
  3. additionThe reaction was poured onto aq. NaHCO3 (10 mL)
  4. extractionextracted with methylene chloride (3×10 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f186d2b622e43ee8adb242000f5a529
Source dataset
uspto-grants-2003_08
Patent number
US06610722B2

Reaction notes

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