Sodium borohydride → HCID 71666214, compound

HRID 624676Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([C:22]2[S:44][C:25]3=[N:26][C:27]([N:31]4[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]4)=[CH:28][C:29](=[O:30])[N:24]3[N:23]=2)[CH:7]=[C:8]([NH:10][C:11](=[O:21])[CH2:12][NH:13]C(OC(C)(C)C)=O)[CH:9]=1)(=[O:3])[CH3:2].C(OC(NCC(NC1C=C(C2SC3=NC(N4CCN(C(OC(C)(C)C)=O)CC4)=CC(=O)N3N=2)C=C(C(O)C)C=1)=O)=O)(C)(C)C.[BH4-].[Na+]>>[NH2:13][CH2:12][C:11]([NH:10][C:8]1[CH:7]=[C:6]([C:22]2[S:44][C:25]3=[N:26][C:27]([N:31]4[CH2:32][CH2:33][NH:34][CH2:35][CH2:36]4)=[CH:28][C:29](=[O:30])[N:24]3[N:23]=2)[CH:5]=[C:4]([CH:1]([OH:3])[CH3:2])[CH:9]=1)=[O:21]

Participants

Reactant 3

HCID 4311764Sodium borohydride

HCID 89705353HCID 89705353, compound

HCID 89711400HCID 89711400, compound

Product 1

HCID 71666214HCID 71666214, compound

Procedure

The compound of this example is prepared as described in Example 13 above except that the acetyl group of tert-butyl 4-(2-(3-acetyl-5-(2-((tert-butoxycarbonyl)amino)-acetamido)phenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate is further reduced to tert-butyl 4-(2-(3-(2-((tert-butoxycarbonyl)amino)acetamido)-5-(1-hydroxyethyl)phenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate using sodium borohydride. The resulting product is then deprotected as described in Step 6 of Example 1. 1H NMR (400 MHz, DMSO-d6) δ 10.73 (s, 1H), 8.95-8.80 (br.s., 2H), 8.16 (t, J=1.8 Hz, 1H), 8.16-8.07 (br.s., 2H), 7.76 (t, J=1.8 Hz, 1H), 7.59 (s, J=1.8 Hz, 1H), 5.61 (s, 1H), 5.50-5.45 (br.s., 1H), 4.83 (q, J=6.7 Hz, 1H), 3.81 (s, 2H), 3.78 (t, J=5.2 Hz, 4H), 3.19 (t, J=5.2 Hz, 4H), 1.36 (d, J=6.7 Hz, 3H); LC/MS: tR=2.417 min; HRMS: m/z (M+H+)=(Calculated for C19H24N7O3S=430.1661).

Sources & evidence

ORD record: ord-72639a55af644943bd9dc3102cb7802d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303044B2

Reaction notes

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