1,2-Dichloroethane → HCID 117748782, compound

HRID 1775862Notes

Reaction equation

HRID 1775862 reaction equation
[C:1]([O:5][C:6](=[O:37])[C@@H:7]([NH:24][C:25](=[O:36])[C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][N:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[C:42]([NH:50][NH2:51])(=[O:49])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>C(Cl)Cl.CN(C1C=CN=CC=1)C.C([O-])(O)=O.[Na+]>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([C:25]([NH:24][C@@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:20]=[CH:19][C:18]([C:21]([NH:51][NH:50][C:42](=[O:49])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:23])=[CH:17][N:16]=3)=[CH:11][CH:10]=2)[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:37])=[O:36])=[CH:31][CH:30]=1)([CH3:34])([CH3:33])[CH3:35]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 240032heptanohydrazideHCID 117740712(S)-2-(4-(3-(tert-butoxy)-2-(4-(tert-butyl)benzamido)-3-oxopropyl)phenyl)pyrimidine-5-carboxylic acid

Product 1

HCID 117748782HCID 117748782, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Prepared using General Procedure 7. Into a stirring solution of (S)-2-(4-(3-(tert-butoxy)-2-(4-(tert-butyl)benzamido)-3-oxopropyl)phenyl)pyrimidine-5-carboxylic acid (50 mg, 0.10 mmol) in DCM (2 mL) were added EDC (34 mg, 0.20 mmol), DMAP (3 mg, 0.02 mmol) and heptanehydrazide (16 mg, 0.11 mmol). After 18 h, the reaction mixture was diluted with NaHCO3 and extracted with DCM (2×). The organic layers were combined, dried (Na2SO4), concentrated and purified by chromatography (EA/Hexane) to provide 38 mg (61%) of tert-butyl (S)-2-(4-(tert-butyl)benzamido)-3-(4-(5-(2-heptanoylhydrazine-1-carbonyl)pyrimidin-2-yl)phenyl)propanoate. LCMS-ESI (m/z) calculated for C36H47BN5O5: 629.8; no m/z observed, tR=3.84 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 9.17 (s, 2H), 8.42 (d, J=8.2 Hz, 2H), 7.69 (d, J=8.4 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.2 Hz, 2H), 6.70 (d, J=7.3 Hz, 1H), 5.01 (dd, J=12.6, 5.8 Hz, 1H), 3.41-3.20 (m, 2H), 2.35 (t, J=7.5 Hz, 2H), 1.81-1.61 (m, 2H), 1.59 (d, J=14.0 Hz, 2H), 1.45 (s, 4H), 1.42-1.22 (m, 18H), 0.88 (t, J=6.8 Hz, 3H).

Workup

  1. customPrepared
  2. extractionextracted with DCM (2×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by chromatography (EA/Hexane)

Sources & evidence

ORD record
ord-fd116598c21d421d89cdda580674ff25
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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